Sodium Hydroxide → 3-(4-Bromo-3-fluorophenyl)prop-2-enoic acid

HRID 1930209Notes

Reaction equation

HRID 1930209 reaction equation
C([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[C:9]([F:14])[CH:8]=1)C.[OH-].[Na+]>CO>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]=[CH:5][C:4]([OH:15])=[O:3])=[CH:8][C:9]=1[F:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67313932Ethyl 3-(4-bromo-3-fluorophenyl)prop-2-enoate

Product 1

HCID 674566403-(4-Bromo-3-fluorophenyl)prop-2-enoic acidYield 84.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.5 g (38.6 mmol) of 3-(4-bromo-3-fluoro-phenyl)-acrylic acid ethyl ester were dissolved in 100 mL of methanol and stirred overnight with 97 mL of aqueous 1 M sodium hydroxide solution. After removal of the methanol in vacuo the residue was acidified with concentrated hydrochloric acid. The precipitate was isolated by suction and dried in vacuo at 50° C. furnishing 8.0 g of 3-(4-bromo-3-fluoro-phenyl)-acrylic acid.

Workup

  1. customAfter removal of the methanol in vacuo the residue
  2. customThe precipitate was isolated by suction
  3. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-ead58592dabe476faca4a17b043d5ef5
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

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