Benzyl Bromide → 2-(3-(Benzyloxy)-4-chlorophenyl)-acetonitrile

HRID 1255560Notes

Reaction equation

HRID 1255560 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1>CC#N>[CH2:24]([O:11][C:3]1[CH:4]=[C:5]([CH2:8][C:9]#[N:10])[CH:6]=[CH:7][C:2]=1[Cl:1])[C:21]1[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 55267733(4-Chloro-3-hydroxy-phenyl)acetonitrile

Product 1

HCID 670440872-(3-(Benzyloxy)-4-chlorophenyl)-acetonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (4-chloro-3-hydroxy-phenyl)acetonitrile (6.2 g, 37 mmol) in CH3CN (80 mL) was added K2CO3 (10.2 g, 74 mmol) and BnBr (7.6 g, 44 mmol). The mixture was stirred at room temperature overnight. The solids were filtered off and the filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel (Petroleum Ether/Ethyl Acetate 50:1) to give 2-(3-(benzyloxy)-4-chlorophenyl)acetonitrile (5.6 g, 60%). 1H NMR (400 MHz, CDCl3) δ 7.48-7.32 (m, 6H), 6.94 (d, J=2 Hz, 2H), 6.86 (dd, J=2.0, 8.4 Hz, 1H), 5.18 (s, 2H), 3.71 (s, 2H).

Workup

  1. filtrationThe solids were filtered off
  2. customthe filtrate was evaporated under vacuum
  3. customThe residue was purified by column chromatography on silica gel (Petroleum Ether/Ethyl Acetate 50:1)

Sources & evidence

ORD record
ord-eeac438afb0b49ae9780ca3e3d46b72b
Source dataset
uspto-grants-2013_06
Patent number
US08461156B2

Reaction notes

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