Boron tribromide → 2-Chloro-4-hydroxybenzenebutanoic acid

HRID 1497529Notes

Reaction equation

HRID 1497529 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][CH2:12][C:13]([O:15]C(C)(C)C)=[O:14].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 90282144HCID 90282144, compound

Product 1

HCID 822677082-Chloro-4-hydroxybenzenebutanoic acidYield 49.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(2-chloro-4-methoxyphenyl)butanoate (1.73 g) in dichloromethane (10.0 mL) were added under ice-cooling, and a 1 M solution of boron tribromide in dichloromethane (12.2 mL), followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure and basified by the addition of a saturated aqueous sodium hydrogen carbonate solution, and 1 M hydrochloric acid was added thereto until the liquid became acidic. The precipitated insoluble material was collected by filtration and dried under reduced pressure to obtain 4-(2-chloro-4-hydroxyphenyl)butanoic acid (647 mg).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionbasified by the addition of a saturated aqueous sodium hydrogen carbonate solution, and 1 M hydrochloric acid
  4. additionwas added
  5. filtrationThe precipitated insoluble material was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d34f5444f6f548fe88070ed68fc8e1b6
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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