Water → 6-Fluoro-2-hydroxy-3-methoxybenzaldehyde

HRID 2110959Notes

Reaction equation

HRID 2110959 reaction equation
B(Cl)(Cl)Cl.[F:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10]([O:14]C)[C:9]([O:16][CH3:17])=[CH:8][CH:7]=1.O>ClCCl>[F:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10]([OH:14])[C:9]([O:16][CH3:17])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25135Boron TrichlorideHCID 107261486-Fluoro-2,3-dimethoxybenzaldehyde

Product 1

HCID 224828186-Fluoro-2-hydroxy-3-methoxybenzaldehydeYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1M boron trichloride in dichloromethane (25 ml; 25 mmol) was added to a solution of 6-fluoro-2,3-dimethoxy-benzaldehyde [Cantrell, Amanda S.; Engelhardt, Per; Hoegberg, Marita; Jaskunas, S. Richard; Johansson, Nils Gunnar; et al.; J. Med. Chem.; 39; 21; 1996; 4261-4274] (4.26 g; 23 mmol) in dichloromethane (30 ml) keeping the reaction temperature at −70 C. The reaction mixture stirred at room temperature overnight and hydrolyzed with water. The organic phase was separated, washed with water and evaporated in vacuc. The residue was chromatographed (silica gel, EA:Hex, 5:1) to give 3.72 g (94%) of 6-fluoro-2-hydroxy-3-methoxy-benzaldehyde as yellow crystals.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. customevaporated in vacuc
  4. customThe residue was chromatographed (silica gel, EA:Hex, 5:1)

Sources & evidence

ORD record
ord-4cf595069d894e2f8f45083b2b5021c4
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

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