Carbon tetrabromide → 4-(Bromomethyl)-2-hydroxybenzonitrile

HRID 379024Notes

Reaction equation

HRID 379024 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>CN(C=O)C.C(Cl)Cl>[Br:32][CH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([OH:1])[CH:9]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 216969742-Hydroxy-4-(hydroxymethyl)benzonitrile

Product 1

HCID 216969934-(Bromomethyl)-2-hydroxybenzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Hydroxy-4-hydroxymethylbenzonitrile (0.20 g, 1.34 mmol) was dissolved in DMF (5 mL)—CH2Cl2(5 mL) and treated with triphenylphosphine (0.53 g, 2.01 mmol) and carbon tetrabromide (0.67 g, 2.01 mmol) at ambient temperature with stirring. After 2 h the reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL), the organic layer separated, dried (MgSO4), and filtered to give the title compound after silica gel chromatography (15% EtOAc/hexane to 25% EtOAc/hexane).

Workup

  1. customAfter 2 h the reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL)
  2. customthe organic layer separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8991a41115b445c2baca422ec49769a8
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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