4-Hydroxybenzaldehyde → 4-[(3-Fluorophenyl)methoxy]benzaldehyde

HRID 853168Notes

Reaction equation

HRID 853168 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br>CN(C)C=O.O>[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromide

Product 1

HCID 8801194-[(3-Fluorophenyl)methoxy]benzaldehydeYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 6.0 g of 4-hydroxy-benzaldehyde and 13.58 g of potassium carbonate in 60 ml of N,N-dimethylformamide was treated dropwise at room temperature with a solution of 11.14 g of 3-fluoro-benzylbromide in 30 ml of N,N-dimethylformamide. After 3 h the reaction mixture was diluted with water and extracted with ether. The organic layer was washed with water, dried over magnesium sulphate and evaporated to yield an oil (9.85 g) which crystallised on standing; MS: m/e=230 (M)+. The crude product was used in the next step without further purification.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-92d42ce24da149d385e5ee5dd40172c4
Source dataset
uspto-grants-2007_08
Patent number
US07253318B2

Reaction notes

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