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

HRID 1847329Notes

Reaction equation

HRID 1847329 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 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-ad0f8747d94c468e9ebc1530c1baedf2
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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