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ChemicalBook CAS DataBase List BENZOIC ACID,4-BROMO-2-METHYL-,METHYL ESTER

BENZOIC ACID,4-BROMO-2-METHYL-,METHYL ESTER synthesis

7synthesis methods
-

Yield:99548-55-7 100%

Reaction Conditions:

with sodium hydrogencarbonate in N,N-dimethyl-formamide at 80;

Steps:

5.5.76.1
5.76 l-(3-CHIX)RO-4-METHYI^PHENYLV3-r2-f2.6-DIOXO-PIPERrom- 3-YU-I-OXO-Z^-DIHYDRO-IH-ISOINDOL-S-YLMETHYLI-TJREA Step 1: A mechanically stirred mixture of 4-bromo-2-methyl-benzoic acid (100 g, 465 mmol), iodomethane (95 g, 670 mmol) and sodium bicarbonate (1 12 g, 1340 mmoi) in DMF (325 mL) was heated at 80 0C overnight. The reaction mixture was cooled to room temperature and partitioned between water (1500 mL) and 4: 1 hexanes:ethyl acetate (1500 mL). The organic layer was washed with water and dried (Na2SO4). The solvent was removed under vacuum to give HO g of 4-bromo-2-methyl-benzoic acid methyl ester as an oil, in 100% yield; 1H NMR δ 2.51 (s, 3H), 3.84 (s, 3H), 7.40-7.78 (m, 3H).

References:

CELGENE CORPORATION WO2008/27542, 2008, A2 Location in patent:Page/Page column 89-90

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