Benzyl Bromide → 4-(Benzyloxy)-3,5-difluorobenzaldehyde

HRID 62834

Reaction equation

HRID 62834 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC#N>[CH2:18]([O:10][C:9]1[C:2]([F:1])=[CH:3][C:4]([CH:5]=[O:6])=[CH:7][C:8]=1[F:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 101925843,5-Difluoro-4-hydroxybenzaldehyde

Product 1

HCID 157140264-(Benzyloxy)-3,5-difluorobenzaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5-Difluoro-4-hydroxy-benzaldehyde obtained in Step A was dissolved in CH3CN (15 mL), and Cs2CO3(6.3 g, 19.23 mmol) was added to the solution. The mixture was cooled to 0˜5° C. Benzylbromide (1.1 mL, 9.23 mmol) was added slowly thereto, and the mixture was stirred at room temperature for 2 hours. After the termination of the reaction, the reactant was filtered and then concentrated under reduced pressure. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/7) to obtain the title compound (1.76 g, 92%).

Workup

  1. temperatureThe mixture was cooled to 0˜5° C
  2. customAfter the termination of the reaction
  3. filtrationthe reactant was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/7)

Sources & evidence

ORD record
ord-a43a6fb9e8be42e3a3e74def7ffb4128
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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