Boron tribromide → (4-Chloro-3-hydroxy-phenyl)acetonitrile

HRID 881066Notes

Reaction equation

HRID 881066 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][C:7]=1[O:15]C>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][C:7]=1[OH:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20460956(4-Chloro-3-methoxyphenyl)acetonitrile

Product 1

HCID 55267733(4-Chloro-3-hydroxy-phenyl)acetonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (16.6 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in DCM (120 mL) at −78° C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice-water. The organic layer was separated and the aqueous layer was extracted with DCM (40 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) δ 7.34 (d, J=8.4 Hz, 1 H), 7.02 (d, J=2.1 Hz, 1 H), 6.87 (dd, J=2.1, 8.4 Hz, 1 H), 5.15 (brs, 1H), 3.72 (s, 2 H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with DCM (40 mL×3)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bde629d4140f4ec0a94e8f6d01f83e8f
Source dataset
uspto-grants-2015_03
Patent number
US08993600B2

Reaction notes

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