Water → (4-Chloro-3-hydroxy-phenyl)acetonitrile

HRID 1908344Notes

Reaction equation

HRID 1908344 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.O>ClCCl>[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

5

Reactant 3

HCID 962WaterHCID 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 (17 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in dichloromethane (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 and water. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (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, 1H), 7.02 (d, J=2.1 Hz, 1H), 6.87 (dd, J=2.1, 8.4 Hz, 1H), 5.15 (brs, 1H), 3.72 (s, 2H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (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-d76c7621ff3543e59d9336a7314ca1b0
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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