Sodium Iodide → 5-Chloro-2-(2,3-difluoro-6-methoxybenzyloxy)anisole

HRID 1512968Notes

Reaction equation

[F:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[CH2:4]Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([O:21][CH3:22])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:4][C:3]2[C:6]([O:11][CH3:12])=[CH:7][CH:8]=[C:9]([F:10])[C:2]=2[F:1])=[C:16]([O:21][CH3:22])[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,3-difluoro-6-methoxybenzyl chloride (7.65 g), 4-chloro-2-methoxyphenol (6.34 g), potassium carbonate (8.29 g) and sodium iodide (1.2 g) in N,N-dimethylformamide (20 mL) was stirred at 80° C. for 2 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with 1 mol/L aqueous sodium hydroxide solution, water and brine successively, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residual solids were suspended in a mixed solvent (n-hexane/diethyl ether=5/1), and collected by filtration. The collected solids were washed with the same solvent, and dried under reduced pressure to give the title compound (8.6 g).

Workup

extractionthe resulting mixture was extracted with diethyl ether
washThe extract was washed with 1 mol/L aqueous sodium hydroxide solution, water and brine successively
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
filtrationcollected by filtration
washThe collected solids were washed with the same solvent
customdried under reduced pressure

Sources & evidence

ORD record: ord-528208a1dfe8437e97748862cb58ae6d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217069B2

Reaction notes

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