Water → 2-(3-Hydroxyphenyl)acetonitrile

HRID 1505115Notes

Reaction equation

HRID 1505115 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 88310(3-Methoxyphenyl)acetonitrile

Product 1

HCID 137810422-(3-Hydroxyphenyl)acetonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-methoxyphenyl)acetonitrile (150 g, 1.03 mol) in CH2Cl2 (1000 mL) was added BBr3 (774 g, 3.09 mol) dropwise at −70° C. The mixture was stirred and warmed to room temperature slowly. Water (300 mL) was added at 0° C. The resulting mixture was extracted with CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude residue was purified by column (Petroleum Ether/EtOAc 10:1) to give (3-hydroxyphenyl)acetonitrile (75.0 g, 55%). 1H NMR (CDCl3, 300 MHz) δ 7.18-7.24 (m, 1 H), 6.79-6.84 (m, 3 H), 3.69 (s, 2 H).

Workup

  1. extractionThe resulting mixture was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe crude residue was purified by column (Petroleum Ether/EtOAc 10:1)

Sources & evidence

ORD record
ord-1ebbb9a932b94b3eb3647687ed5b459e
Source dataset
uspto-grants-2015_12
Patent number
US09216969B2

Reaction notes

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