Boron tribromide → (2-Bromo-4-hydroxyphenyl)acetic acid

HRID 1026238Notes

Reaction equation

HRID 1026238 reaction equation
BrB(Br)Br.[Br:5][C:6]1[CH:11]=[C:10]([O:12]C)[CH:9]=[CH:8][C:7]=1[CH2:14][C:15]([OH:17])=[O:16]>ClCCl>[Br:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:7]=1[CH2:14][C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

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

Product 1

HCID 24721648(2-Bromo-4-hydroxyphenyl)acetic acidYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (1.0 M, 150 mL) of tribromoborane was added dropwise to a solution of (2-bromo-4-methoxyphenyl)acetic acid (15.0 g) in dichloromethane (160 mL) at room temperature, and the reaction mixture was refluxed for 3 hr, allowed to cool to room temperature, and poured into ice water. The mixture was extracted with ethyl acetate, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained yellow solid was collected by filtration and washed with hexane-diethyl ether to give the title compound (10.3 g).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. filtrationThe obtained yellow solid was collected by filtration
  7. washwashed with hexane-diethyl ether

Sources & evidence

ORD record
ord-3f38e7a0d6fe492bac206d1f261e2f0d
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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