Vanillin → 4-[(2-fluorobenzyl)oxy]-3-methoxybenzaldehyde

HRID 2218552Notes

Reaction equation

HRID 2218552 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[OH:20])[CH:15]=[O:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][O:20][C:19]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[O:11][CH3:10]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotoluene

Product 1

HCID 7354584-[(2-fluorobenzyl)oxy]-3-methoxybenzaldehydeYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.5M solution of 1-bromomethyl-2-fluoro-benzene (1.5 mg, 8 mmol) in DMF was added dropwise to a suspension of 3-methoxy-4-hydroxy-benzaldehyde (1.1 g, 7.3 mmol), K2CO3 (1.51 g, 11 mmol) and KI (120 mg, 7.3 mmol) in DMF (100 ml). The reaction mixture was treated as described in Example 4. The residue was purified on silica gel, obtaining 1.89 g (quantitative yield) of the title compound, yield 100%.

Workup

  1. additionThe reaction mixture was treated
  2. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-73d9aac700084d7caf32eb5a268a945d
Source dataset
uspto-grants-2008_08
Patent number
US07411091B2

Reaction notes

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