ChemicalBook CAS DataBase List 4-Bromo-3-methylaniline

4-Bromo-3-methylaniline synthesis

9synthesis methods

Product Name:4-Bromo-3-methylaniline
CAS Number:6933-10-4
Molecular formula:C7H8BrN
Molecular Weight:186.05

7149-70-4

6933-10-4

General procedure for the synthesis of 4-bromo-3-methylaniline from 2-bromo-5-nitrotoluene: First, N-(4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-methylphenyl)methanesulfonamide (4-bromo-3-methylphenyl)amine was prepared. Subsequently, activated Raney nickel (0.4 g) was added to a suspension of 1-bromo-2-methyl-4-nitrobenzene (4 g, 18.51 mmol) in 200 mL of methanol. The mixture was stirred under hydrogen atmosphere (30 psi) for 3 hours. Upon completion of the reaction, the reaction mixture was filtered through Celite, the solvent was removed under reduced pressure and the residue was dried under vacuum to afford 4-bromo-3-methylaniline (3.4 g, 99% yield) as a white solid.1H-NMR data (CDCl3): δ 2.28 (s, 3H), 3.39 (brs, 2H), 6.38 (d, J = 8Hz, 1H), and 6.55 (s, 1H), 7.27 (d, J = 8Hz, 1H).

108-44-1 Synthesis

108-44-1
379 suppliers
$9.00/1g

6933-10-4
203 suppliers
$7.00/5g

Yield:6933-10-4 95%

Reaction Conditions:

with o-xylylene bis(triethylammonium tribromide) in acetonitrile at 20; for 0.0833333 h;regioselective reaction;

Steps:

3.3. General Procedure for Bromination of AromaticCompounds
General procedure: To a magnetic solution of aromatic compound (1 mmol)in acetonitrile (5 mL), OXBTEATB (0.233 g, 0.5 mmol) wasadded and stirred at room temperature for the appropriatetime (Table 1). The reaction was monitored by TLC (eluent:n-hexane/ethyl acetate: 5/1). The reaction mixture was transferredinto a separatory funnel after filtration of OXBTEABand was extracted with water (15 mL) and dichloromethane(20 mL). The organic layer was dried over anhydrousNa2SO4, and the solvent was concentrated in a rotary evaporator.The crude product was purified by passing it over acolumn of silica gel using a mixture of n-hexane and ethylacetate as the eluent. In order to regenerate the reagent, whitesolid was treated with liquid bromine. All the product structureswere confirmed by comparison of melting point or 1HNMR spectra with ones reported in the literature [29a-29e].

References:

Hemati, Roya;Shahvelayati, Ashraf S.;Yadollahzadeh, Khadijeh [Letters in Organic Chemistry,2018,vol. 15,# 8,p. 682 - 687]

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7149-70-4 Synthesis

7149-70-4
189 suppliers
$9.00/1g

6933-10-4
203 suppliers
$7.00/5g

References