Methane, dichloromethoxy- → 4-broMo-2-fluoro-5-Methoxy-benzaldehyde

HRID 2236485Notes

Reaction equation

HRID 2236485 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[CH3:11][O:12]C(Cl)Cl>Cl[Ti](Cl)(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[CH:4][C:5]([CH:11]=[O:12])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 1362922-Bromo-4-fluoroanisole

Product 1

HCID 575272884-broMo-2-fluoro-5-Methoxy-benzaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a N2 purged flask is added TiCl4 (0.44 mL) followed by 2-Bromo-4-fluoro-1-methoxy-benzene (400 mg, 1.95 mmol). The stirred mixture is cooled in an ice water bath and treated dropwise with 1,1-dichloromethyl methyl ether (0.35 mL, 1.95 mmol). After stirring for 90 minutes, the resulting slurry is treated with CH2Cl2 (200 mL) and reaction is allowed to warm up to room temperature. After passing through a column, the title compound is isolated (220 mg, 48%). MS (ESI): 232.9 (M+1)+1.

Workup

  1. temperatureThe stirred mixture is cooled in an ice water bath

Sources & evidence

ORD record
ord-d79b20c596fd4a959662997079ab213b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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