S-2-Pyridinyl 4-bromo-2-chlorobenzenecarbothioate → 1-(4-Bromo-2-chlorophenyl)ethan-1-one

HRID 858573Notes

Reaction equation

N1C=CC=CC=1S[C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[Cl:16].[CH3:18][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([C:8](=[O:17])[CH3:18])=[C:10]([Cl:16])[CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

4-Bromo-2-chloro-thiobenzoic acid S-pyridin-2-yl ester (1.86 g, 5.66 mmol) from Step 1 above was dissolved in dry THF (30 mL) and cooled to −78° C. A solution of methyl magnesium bromide in 75:25 toluene/THF (1.4 M, 4.45 mL, 6.23 mmol) was added dropwise. After stirring 35 min, the cooling bath was removed. The reaction mixture was quenched with saturated 1N HCl and extracted with EtOAc (30 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4 and evaporated. The residue was purified by flash column chromatography (10% EtOAc in hexanes) to give the product (1.05 g, 80%) as a colorless oil.

Workup

customthe cooling bath was removed
customThe reaction mixture was quenched with saturated 1N HCl
extractionextracted with EtOAc (30 mL)
washThe organic phase was washed with brine (50 mL)
dry with materialdried over Na2SO4
customevaporated
customThe residue was purified by flash column chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-6e62ab795fa049dea8512350ba432d66
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Reaction notes

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