ChemicalBook CAS DataBase List 3-BROMO-2-METHYL-BENZOIC ACID METHYL ESTER

3-BROMO-2-METHYL-BENZOIC ACID METHYL ESTER synthesis

10synthesis methods

Product Name:3-BROMO-2-METHYL-BENZOIC ACID METHYL ESTER
CAS Number:99548-54-6
Molecular formula:C9H9BrO2
Molecular Weight:229.07

76006-33-2

74-88-4

3-BROMO-2-METHYL-BENZOIC ACID METHYL ESTER

99548-54-6

3-Bromo-2-methylbenzoic acid (16 g, 74.4 mmol) and iodomethane (21.2 g, 148.8 mmol) were reacted in DMF (160 mL) in the presence of sodium bicarbonate (12.5 g, 148.8 mmol). The reaction mixture was heated and stirred at 60 °C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and slowly poured into ice water (400 mL). The aqueous phase was extracted with ethyl acetate (4 x 100 mL) and the organic phases were combined. The organic phase was washed sequentially with water (3 x 100 mL) and saturated saline (100 mL) and then dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give methyl 3-bromo-2-methylbenzoate (17.6 g, 100% yield) as an oil. The product was characterized by 1H NMR (CDCl3): δ 7.70 (t, J = 7.6 Hz, 2H), 7.08 (t, J = 7.9 Hz, 1H), 3.90 (s, 3H), 2.67 (s, 3H).

67-56-1 Synthesis

67-56-1
803 suppliers
$7.29/5ml-f

76006-33-2 Synthesis

76006-33-2
333 suppliers
$10.00/5g

99548-54-6
180 suppliers
$5.00/1g

Yield:99548-54-6 99%

Reaction Conditions:

with thionyl chloride at 70; for 1.5 h;

Steps:

112.1
To a mixture of 3-bromo-2-methylbenzoic acid (5.0 g, 23 mmol) in MeOH (80 mL) was added 50C12 (11.0 g, 93 mmol) at 20°C. The mixture was stirred for 1.5h at 70°C. Thevolatiles were removed and the residue was taken up by EtOAc (100 mL), which was washed sequentially with saturated NaHCO3 and brine (each 100 mL). The EtOAc layer was dried over Na2504, concentrated and the residue was purified by flash column chromatography to give methyl 3-bromo-2-methylbenzoate (5.3g, 99% yield) as a red solid.

References:

RQX PHARMACEUTICALS, INC.;GENENTECH, INC.;CHEN, Yongsheng;SMITH, Peter Andrew;ROBERTS, Tucker Curran;HIGUCHI, Robert I.;PARASELLI, Prasuna;KOEHLER, Michael F. T.;SCHWARZ, Jacob Bradley;CRAWFORD, James John;LY, Cuong Q.;HANAN, Emily J.;HU, Huiyong;YU, Zhiyong WO2017/84630, 2017, A1 Location in patent:Paragraph 00545

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76006-33-2 Synthesis

76006-33-2
333 suppliers
$10.00/5g

74-88-4
348 suppliers
$15.00/10g

99548-54-6
180 suppliers
$5.00/1g

References

67-56-1 Synthesis

67-56-1
803 suppliers
$7.29/5ml-f