Dimethylformamide → 4-(Bromomethyl)-2-hydroxybenzonitrile

HRID 1585902Notes

Reaction equation

HRID 1585902 reaction equation
OC[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1O.C(Cl)Cl.[C:15]([Br:19])(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=[O:43])C>>[Br:19][CH2:15][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([OH:43])[CH:4]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18779740HCID 18779740, compound

Product 1

HCID 216969934-(Bromomethyl)-2-hydroxybenzonitrile

Procedure

4-Hydroxymethyl-3-hydroxybenzonitrile (0.20 g, 1.34 mmol) was dissolved in DMF (5 mL): CH2Cl2 (5 mL), treated with CBr4 (0.666 g, 2.01 mmol) and Ph3P (0.527 g, 2.01 mmol), and stirred for 1.5 hr at ambient temperature. The reaction mixture was partitioned between EtOAc (100 mL)--H2O (100 mL), the organic layer separated, dried (MgSO4), filtered, and concentrated to give the title compound after chromatography (SiO2, 15% EtOAc in hexane).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (100 mL)
  2. customH2O (100 mL), the organic layer separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b952bf7f30ca4bf3be27c14aa0baffb5
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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