Ammonium Chloride → HCID 118492125, compound

HRID 711340Notes

Reaction equation

HRID 711340 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)[CH:5]=[N:6][S@:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8].[CH:20]([Mg]Br)=[CH2:21].[NH4+].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C@H:5]([NH:6][S@:7]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8])[CH:20]=[CH2:21])[CH:13]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:15]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 118492077HCID 118492077, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 118492125HCID 118492125, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-N-(3-bromo-5-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamide (20 g, 56.1 mmol) in DCM (300 mL) was drop wise added vinylmagnesium bromide (84 mL, 1 M in THF, 84 mmol) at −60° C. The reaction mixture was stirred at room temperature for 5 h and poured into aqueous NH4Cl solution. The resulting mixture was extracted with DCM (2×100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous MgSO4, and then concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1) to give the title compound (12 g, yield: 56%); m/z (ES+): 384 [M+H]+.

Workup

  1. customat −60° C
  2. extractionThe resulting mixture was extracted with DCM (2×100 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1)

Sources & evidence

ORD record
ord-e4f46ed8beb546eeabb28eaff21e0969
Source dataset
uspto-grants-2015_11
Patent number
US09181259B2

Reaction notes

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