Water → Ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-hydroxy-phenyl]methylamino]phenoxy]acetate

HRID 1771675Notes

Reaction equation

[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([O:23]C)[CH:20]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[CH:18]=2)=[C:13]([F:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[Al+3].[Cl-].[Cl-].[Cl-].C(S)C.O>C(Cl)Cl>[F:1][C:2]1[C:14]([NH:15][CH2:16][C:17]2[CH:22]=[C:21]([OH:23])[CH:20]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[CH:18]=2)=[C:13]([F:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-[2,4-difluoro-3-[[3-(3-fluorophenyl)-5-methoxy-phenyl]methylamino]phenoxy]acetate (400 mg, 0.9 mmol, 1.0 eq) and AlCl3 (718 mg, 5.4 mmol, 6.0 eq) in DCM (10 mL) at 0° C. was added ethanethiol (315 mg, 5.4 mmol, 6.0 eq) under N2. The reaction mixture was stirred at 0° C. for 30 min. The resulting mixture was poured into water and extracted with EtOAc. The organic extract was washed with brine, dried (Na2SO4), filtered, evaporated in vacuo and the crude residue obtained purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title compound as an oil (260 mg, 67%).

Workup

extractionextracted with EtOAc
extractionThe organic extract
washwas washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customthe crude residue obtained
custompurified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4)

Sources & evidence

ORD record: ord-0c7e878ea4fd40f1946aa3e9c73c97b2
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249085B2

Reaction notes

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