4-BROMO-2-(CARBOXYMETHYL)BENZOIC ACID synthesis

7synthesis methods

Product Name:4-BROMO-2-(CARBOXYMETHYL)BENZOIC ACID
CAS Number:943749-63-1
Molecular formula:C9H7BrO4
Molecular Weight:259.05

34598-49-7 Synthesis

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Yield:-

Reaction Conditions:

Stage #1:5-Bromo-1-indanone with sodium methylate;oxalic acid diethyl ester in toluene at 0 - 20; for 1.5 h;
Stage #2: with potassium hydroxide;dihydrogen peroxide in methanol;water at 20 - 64; for 17 h;
Stage #3: with hydrogenchloride in methanol;tert-butyl methyl ether;water

Steps:

17.i
A solution of 5-bromo-1-indanone (25 g) and diethyl oxalate (27.7 g) in toluene (500 ml_) was added to a suspension of sodium methoxide (13.1 g) in toluene (50 ml_) at O⁰C. The mixture was warmed to room temperature and stirred for 90 minutes. The solvent was removed and the residue suspended in methanol (80OmL). Potassium hydroxide (53.1 g) was added portionwise keeping the temp below 50⁰C. Hydrogen peroxide solution (30% w/w, 135 ml_) was then added keeping the temperature below 64⁰C, the reaction mixture was then stirred at room temperature for 17 hours. Sodium sulfite (5% aqueous solution) was added and the reaction stirred for 30 minutes. The reaction mixture was filtered and the filtrate was reduced to half volume then washed with 2-methoxy-2-methyl-propane. The aqueous layer was then acidified with hydrochloric acid and extracted into ethyl acetate. The organic phase was dried, filtered and evaporated then triturated with diethyl ether to yield sub-title compound (9.Og).¹H NMR DMSOd₆ 7.82 (1H, d), 7.62 (1H, d), 7.59 (1H, dd), 3.95 (2H, s).

References:

ASTRAZENECA AB;ASTRAZENECA UK LIMITED WO2008/122765, 2008, A1 Location in patent:Page/Page column 101

38568-41-1 Synthesis