Hydrogen Bromide → [2-(Bromomethyl)phenyl]acetic acid
Reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3](=[O:11])[O:2]1.[BrH:12]>O>[Br:12][CH2:1][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:4][C:3]([OH:2])=[O:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Isochromanone (30 g), Mann, F. G. and Stewart, F. H., Journal of the Chemical Society 2819 (1954) is added with swirling to 150 ml of hydrobromic acid (48%) at 80° C. The resulting mixture is then heated on a steam bath with occasional swirling for 10 min and thereafter poured into a mixture of crushed ice and water (750 g). The resulting mixture is then extracted with ethyl acetate and the ethyl acetate extracts washed with a mixture of water and brine (1:1) and dried over magnesium sulfate. Concentration under reduced pressure yields a residue of crude o-(bromomethyl)phenylacetic acid. (Crystallization of the crude product from methylene chloride yields a product with melting point 130°-131° C. and a C:H ratio of 46.90:4.09). The crude o-(bromomethyl)phenylacetic acid, 400 ml of benzene and 38 g of triphenylphosphine is stirred at 80° C. for 5 hr and cooled and filtered to yield 57 g of title product, melting point 248°-249° C. The C:H:Br:P ratio is 66.22:4.94:16.16:6.49.
Workup
- addition, Journal of the Chemical Society 2819 (1954) is added
- temperatureThe resulting mixture is then heated on a steam bath
- extractionThe resulting mixture is then extracted with ethyl acetate
- washthe ethyl acetate extracts washed with a mixture of water and brine (1:1)
- dry with materialdried over magnesium sulfate
- concentrationConcentration under reduced pressure
Sources & evidence
- ORD record
- ord-887c62ed1392460b98d1e55a49a27a5b
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04281113
Reaction notes
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