N-methoxy-N-methyl-4-(pentafluoro-lambda6-sulfanyl)benzamide → 1-[4-(Pentafluoro-lambda6-sulfanyl)phenyl]ethan-1-one

HRID 1523309Notes

Reaction equation

CON(C)[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.[CH3:19][Li]>C1COCC1>[F:12][S:11]([F:16])([F:15])([F:14])([F:13])[C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:17])[CH3:19])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-methoxy-N-methyl-4-(pentafluoro-λ6-sulfanyl)benzamide (Preparation 42, 3.0 g, 10.3 mmol) in THF (100 mL) at 0° C. was added drop-wise methyl lithium (1.5M solution, 10.3 mL, 15.5 mmol). The reaction was stirred at 0° C. for 2 hours, then quenched with a saturated aqueous solution of ammonium acetate. The reaction was extracted with ethyl acetate and dried over MgSO4 before concentrating in vacuo to afford the title compound that was used without further purification.

Workup

customquenched with a saturated aqueous solution of ammonium acetate
extractionThe reaction was extracted with ethyl acetate
dry with materialdried over MgSO4
concentrationbefore concentrating in vacuo

Sources & evidence

ORD record: ord-0c2e418a45504bc3aba04b33a229415d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079878B2

Reaction notes

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