2-Nitrobenzenesulfonyl chloride → 2-(5-Bromo-2-fluorophenyl)-2-difluoromethyl-1-(2-nitro-benzenesulfonyl)-aziridine

HRID 221743Notes

Reaction equation

[NH2:1][C:2]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[F:15])([CH:5]([F:7])[F:6])[CH2:3]O.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](Cl)(=[O:27])=[O:26])([O-:18])=[O:17].C(=O)([O-])O.[K+]>C(#N)C>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([F:15])=[C:8]([C:2]2([CH:5]([F:7])[F:6])[CH2:3][N:1]2[S:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N+:16]([O-:18])=[O:17])(=[O:26])=[O:27])[CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-Amino-2-(5-bromo-2-fluoro-phenyl)-3,3-difluoro-propan-1-ol (13.04 g, 45.9 mmol) [examples 42 step d)] was dissolved in 261 mL acetonitrile, 2-nitrobenzenesulfonyl chloride (22.38 g, 101 mmol) and potassium hydrogencarbonate (13.79 g, 138 mmol) were added. The mixture was heated to 80° C. and stirred over night. After this period, the reaction mixture was cooled down and partitioned between saturated aqueous NaHCO3 solution and TBME. The layers were separated, washed with brine and TBME. The combined organic layers were dried over MgSO4.H2O and evaporated. The crude product was purified on a silica gel column by eluting with hexane/dichloromethane 2/1->1/2 to give 7.71 g of the title compound as white crystals.

Workup

waitAfter this period
temperaturethe reaction mixture was cooled down
custompartitioned between saturated aqueous NaHCO3 solution and TBME
customThe layers were separated
washwashed with brine and TBME
dry with materialThe combined organic layers were dried over MgSO4.H2O
customevaporated
customThe crude product was purified on a silica gel column
washby eluting with hexane/dichloromethane 2/1->1/2

Sources & evidence

ORD record: ord-f51d69817a754bb9bb0c1befa82f8335
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207164B2

Reaction notes

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