Benzyl Bromide → Benzaldehyde, 5-bromo-3-fluoro-2-(phenylmethoxy)-

HRID 1396575Notes

Reaction equation

HRID 1396575 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:12]([O:10][C:5]1[C:4]([F:11])=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 27792765-Bromo-3-fluoro-2-hydroxybenzaldehyde

Product 1

HCID 86630410Benzaldehyde, 5-bromo-3-fluoro-2-(phenylmethoxy)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Bromo-3-fluoro-2-hydroxy-benzaldehyde (5 g, 22.8 mmol) in DMF (100 ml) is added benzyl bromide (5.7 ml, 48 mmol) and cesium carbonate (11.9 g, 37 mmol). The reaction mixture is stirred at room temperature for 20 hours then diluted with water (150 ml) and extracted with EtOAc (2×150 ml), the organic portions are combined, washed with brine (50 ml), dried over MgSO4 and concentrated in vacuo to give a waxy off-white solid. The solid is stirred in iso-hexanes (30 ml) for 30 minutes, filtered and dried under vacuum to afford the title compound.

Workup

  1. extractionextracted with EtOAc (2×150 ml)
  2. washwashed with brine (50 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a waxy off-white solid
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-7826c9ee850c496f931d0aba92e76347
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

Loading…