ChemicalBook CAS DataBase List 2-Bromo-5-methylbenzenamine

2-Bromo-5-methylbenzenamine synthesis

7synthesis methods

Product Name:2-Bromo-5-methylbenzenamine
CAS Number:53078-85-6
Molecular formula:C7H8BrN
Molecular Weight:186.05

5326-34-1

53078-85-6

Preparation Example 1: General procedure for the synthesis of 2-bromo-5-methylaniline 1. 4-Bromo-3-nitrotoluene (60.35 g, 279 mmol), 5 wt% platinum-carbon catalyst (1.09 g, 0.28 mmol), and triethylamine (112.93 g, 1116 mmol) were added sequentially to the reaction flask. 2. the reaction mixture was heated to 100 °C and 99% formic acid (42.39 g, 921 mmol) was added slowly and dropwise over a period of 20 minutes. 3. The reaction temperature was maintained with continuous stirring for 12 hours. 4. Upon completion of the reaction, cooled to room temperature, ethyl acetate (100 mL) and water (100 mL) were added to the reaction mixture with thorough stirring. 5. Filter through diatomaceous earth to remove the platinum carbon catalyst. 6. Add ethyl acetate (200 mL) and water (100 mL) to the filtrate and extract. 7. The organic phase was separated and washed with deionized water (300 mL x 3 times). 8. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the target product 2-bromo-5-methylaniline (51.30 g, 276 mmol) in 99% yield. 9. The structure of the product was confirmed by 1H-NMR (270 MHz, CDCl3): δ (ppm) 7.260 (1H, d), 6.583 (1H, ... (data not provided in full)).

5326-34-1 Synthesis

5326-34-1
264 suppliers
$6.00/5g

53078-85-6
203 suppliers
$6.00/1g

Yield:53078-85-6 99%

Reaction Conditions:

with formic acid;triethylamine;platinum on carbon at 100; for 12.3333 h;

Steps:

1 Synthesis of 2-bromo-5-methylaniline
Production Example 1 Synthesis of 2-bromo-5-methylaniline 4-Bromo-3-nitrotoluene (60.35 g, 279 mmol), 5% by weight platinum carbon (1.09 g, 0.28 mmol) and triethylamine (112.93 g, 1116 mmol) were stirred under heating at 100° C., to which formic acid (99%) (42.39 g, 921 mmol) was added dropwise over 20 minutes. After stirring for 12 hours, it was brought back to room temperature, and then 100 ml of ethyl acetate and 100 ml of water were added thereto. After stirring well, it was filtered through celite to remove platinum carbon. By further adding 200 ml of ethyl acetate and 100 ml of water, it was extracted, the organic phase was washed with water (300 ml*3 times), and dried on magnesium sulfate. The solvent was evaporated to obtain 2-bromo-5-methylaniline (51.30 g, 276 mmol). The yield was 99%. ¹H-NMR (270 MHz, CDCl₃) δ(ppm): 7.260 (1H, d), 6.583 (1h

References:

Saitoh, Hiroshi;Mizuno, Tsuyoshi;Tsuchiya, Naoki US2003/191325, 2003, A1 Location in patent:Page/Page column 8

FullText

5326-34-1 Synthesis

5326-34-1
264 suppliers
$6.00/5g