Water → (2-Bromo-4-hydroxyphenyl)acetic acid

HRID 1026350Notes

Reaction equation

HRID 1026350 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].BrB(Br)Br.O>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 39636682-Bromo-4-methoxyphenylacetic acid

Product 1

HCID 24721648(2-Bromo-4-hydroxyphenyl)acetic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-4-methoxyphenyl)acetic acid (0.49 g) in dichloromethane (5 mL) was added a solution of tribromoborane (5 mL) dropwise at room temperature. The mixture was refluxed for 3 hr. After cooling to room temperature, the mixture was poured into iced water. The organic layer was separated, and the water layer was extracted by ethyl acetate (30 mL×3). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue was washed with ether to give the title compound (0.45 g).

Workup

  1. temperatureThe mixture was refluxed for 3 hr
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted by ethyl acetate (30 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. washThe residue was washed with ether

Sources & evidence

ORD record
ord-7ca949c592364508b5e8353ff6acfa05
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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