Benzyl Bromide → 4-(Benzyloxy)-2-chlorobenzaldehyde

HRID 62891

Reaction equation

HRID 62891 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC#N>[CH2:17]([O:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([Cl:1])[CH:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 1853632-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 140340774-(Benzyloxy)-2-chlorobenzaldehydeYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-4-hydroxy-benzaldehyde obtained in Step A was dissolved in CH3CN (20 mL). After Cs2CO3(8.7 g, 0.027 mol) was added thereto, benzyl bromide (1.5 mL, 0.013 mol) was added thereto, and the mixture was stirred at room temperature for 2 hours. After the termination of the reaction, the reactant was filtered by using celite, concentrated under reduced pressure, and purified by column chromatography (eluent, EtOAc/Hex=1/5) to obtain the title compound (1.89 g, 59%).

Workup

  1. customAfter the termination of the reaction
  2. filtrationthe reactant was filtered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (eluent, EtOAc/Hex=1/5)

Sources & evidence

ORD record
ord-558ef29b1e9c468b94748d66fc4d701c
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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