Carbon tetrabromide → [3-(Bromomethyl)phenyl]acetonitrile

HRID 1866912Notes

Reaction equation

HRID 1866912 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.C(Br)(Br)(Br)[Br:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Br:13][CH2:2][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 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22050157[3-(Hydroxymethyl)phenyl]acetonitrile

Product 1

HCID 14774147[3-(Bromomethyl)phenyl]acetonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of (3-hydroxymethylphenyl)acetonitrile (0.97 g, 7.3 mmol) in THF (35 mL) was added CBr4 (2.5 g, 7.7 mmol) and Ph3P (2.0 g, 7.7 mmol), and the reaction mixture was stirred for 3 h. The reaction mixture was filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, eluent 1:9 to 1:4 EtOAc/hexanes) provided (3-bromomethylphenyl)acetonitrile as a clear oil (0.89 g, 58%): 1H NMR (300 MHz, MeOD) δ 7.47-7.29 (m, 1H), 7.27 (s, 1H), 6.97 6.82 (m, 1H), 4.87 (s, 2H), 3.91 (s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash column chromatography (silica, eluent 1:9 to 1:4 EtOAc/hexanes)

Sources & evidence

ORD record
ord-fe734df2eece45c4b44cb579f7e6a8df
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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