Bromine → HCID 18415131, compound

HRID 991983Notes

Reaction equation

HRID 991983 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Br:13]Br>C(O)(=O)C.O>[Br:13][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:3]=[C:2]([Cl:1])[C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 24408BromineHCID 1185343-Chloro-4-hydroxyphenylacetic acid

Product 1

HCID 18415131HCID 18415131, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3-chloro-4-hydroxyphenylacetic acid (2.5 g) in glacial acetic acid (35 mL) was added 0.8 mL of neat bromine carefully while stirring. The mixture was stirred in dark at ambient temperature for 51 h. The resulting mixture was diluted with water, extracted with ethyl acetate, dried and concentrated in vacuo to afford 3-bromo-5-chloro-4-hydrox-yphenylacetic acid. This crude product was dissolved in methanol (15 mL), treated with concentrated sulfuric acid (1 mL) carefully, stirred at reflux for 18 h. Cooled reaction mixture was concentrated under reduced pressure, diluted with water carefully, extracted with dichloromethane. The combined organic layers were dried and concentrated. Flash column chromatography on silica gel with ethyl acetate/hexane (0-50% gradient elution) afforded 3-bromo-5-chloro-4-hydroxyphenylacetic acid methyl ester (2.5 g, 68%).

Workup

  1. stirringThe mixture was stirred in dark at ambient temperature for 51 h
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b32975b9e1e349baa3c8c1df216ccaec
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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