Water → 5-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenylacetic acid

HRID 730177Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=2[CH3:21])=[C:6]([CH2:8][C:9]#N)[CH:7]=1.S(=O)(=O)(O)[OH:23].[OH2:27]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=2[CH3:21])=[C:6]([CH2:8][C:9]([OH:23])=[O:27])[CH:7]=1

Participants

Conditions

Temperature: 115 °C

Procedure

A stirred mixture of 5-bromo-2-[2-(3-methoxy-2-methyl-phenyl)-ethyl]-phenylacetonitrile 10 (8.57 g; 24.9 mmol) in water and acetic acid was treated drop-wise with concentrated sulfuric acid (8.5 mL), heated at 115° C. for 5 hours, cooled to ambient temperature, diluted with water and extracted with chloroform. The extracts were combined, dried over Na2SO4, and evaporated. The resultant residue was purified on a silica gel column (hexane and ethyl acetate (7:3) as eluent) to give compound 11, 5.0 g, 55% yield.

Workup

temperaturecooled to ambient temperature
extractionextracted with chloroform
dry with materialdried over Na2SO4
customevaporated
customThe resultant residue was purified on a silica gel column (hexane and ethyl acetate (7:3) as eluent)

Sources & evidence

ORD record: ord-fe6fe04636734c8580698564378fc7b9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582667B2

Reaction notes

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