Carbon tetrabromide → 4-(2-Bromoethyl)benzonitrile

HRID 2173211Notes

Reaction equation

HRID 2173211 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C(Cl)Cl>[Br:32][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 128865484-(2-Bromoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(2Hydroxyethyl)benzonitrile (3.0 g, 20 mmol) was combined with triphenylphosphine (6.42 g, 24.5 mmol) imidazole (1.39 g, 20.4 mmol) and carbon tetrabromide (8.11 g, 24.5 mmol) in DCM (10 mL) and stirred at 0° C., monitoring the reaction progress to completion by TLC. Silica gel was added to the mixture and the solvent was removed. Purification by MPLC eluting with 20% ethyl acetate/hexanes afforded the tide compound.

Workup

  1. additionSilica gel was added to the mixture
  2. customthe solvent was removed
  3. customPurification by MPLC
  4. washeluting with 20% ethyl acetate/hexanes
  5. customafforded the tide compound

Sources & evidence

ORD record
ord-a081bb54c1a047c79b144a20f6737053
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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