Lawesson's reagent → 4-bromo-2-fluoro-N-methylbenzothioamide

HRID 537177Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=O)=[C:4]([F:12])[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[S:22])[NH:8][CH3:9])=[C:4]([F:12])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (500 mg, 2 mmol) and Lawesson reagent (872 mg, 2.16 mmol) in toluene (10 mL) was heated to 100° C. and stirred for 4 hours. The reaction was cooled to room temperature, diluted with toluene, and filtered. The filtrate was concentrated and purification of the residue by flash column chromatography (0-20% ethyl acetate/heptanes) gave the title compound (520 mg, 97%) as a yellow solid. +ESI (M+H+1) 250.1; 1H NMR (400 MHz, CDCl3, δ): 8.09 (t, J=8.58 Hz, 1H), 8.03 (br. s., 1H), 7.35 (dd, J=8.19, 2.15 Hz, 1H), 7.27 (dd, J=11.41, 1.85 Hz, 1H), 3.36 (dd, J=4.88, 0.78 Hz, 3H).

Workup

temperatureThe reaction was cooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated
custompurification of the residue by flash column chromatography (0-20% ethyl acetate/heptanes)

Sources & evidence

ORD record: ord-44879c267dbf4379b5a3d3b5ddef69f4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859773B2

Reaction notes

Loading…