Ethylacetate heptane → (R)-N-((S)-1-(4-bromo-2,5-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

HRID 57427Notes

Reaction equation

[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:5](/[CH:6]=[N:7]/[S@@:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])=[C:4]([F:17])[CH:3]=1.[CH3:18][Mg]Br.CCOC(C)=O.CCCCCCC>C(Cl)Cl.CCOCC>[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:5]([C@@H:6]([NH:7][S@@:8]([C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9])[CH3:18])=[C:4]([F:17])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (R,E)-N-(4-bromo-2,5-difluorobenzylidene)-2-methylpropane-2-sulfinamide (7.2 g, 22.2 mmol in CH2Cl2 (200 mL) cooled to 0° C. (water/ice bath) under nitrogen, was added 3M methyl magnesium bromide (29.6 mL, 89 mmol) in Et2O. Reaction mixture allowed to stir for 5 hours at 0° C. then quenched with the slow addition of a saturated solution of NH4Cl. Aqueous mixture adjusted to pH 8 with HCl (1 N) and extracted with DCM. Organic phases combined, washed with water, brine, dried (Na2SO4), filtered and concentrated onto silica gel. Silica gel column chromatography (EtOAc/Heptane 30 to 100%) provided (R)—N—((S)-1-(4-bromo-2,5-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (6.86 g, 20.2 mmol, 91% yield) LCMS m/z 342.1 (M+H)+, Rt 0.96 min.

Workup

customReaction mixture
customthen quenched with the slow addition of a saturated solution of NH4Cl
extractionextracted with DCM
washwashed with water, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated onto silica gel

Sources & evidence

ORD record: ord-fcf99e8a98824f6ab2a801c98bca4c2f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434719B2

Reaction notes

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