Methanesulfonyl chloride → (3-Phenylbenzo[b]thiophen-2-yl)methyl methanesulfonate

HRID 242858Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([C:12]2[C:13]3[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=3[S:15][C:16]=2[CH2:17][OH:18])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CS(Cl)(=O)=O>[CH3:1][S:2]([O:18][CH2:17][C:16]1[S:15][C:14]2[CH:19]=[CH:20][CH:21]=[CH:22][C:13]=2[C:12]=1[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonyl chloride (127 μL, 1.63 mmol) was added dropwise to a solution of (3-phenylbenzo[b]thiophen-2-yl)methanol (356 mg, 1.48 mmol) and DIPEA (322 μL, 1.85 mmol) in anhydrous DCM (10 mL) at 0° C. Stirring at 0° C. was continued for 15 min, then the mixture was slowly warmed to RT. After 2.5 h stirring at RT, additional methanesulfonyl chloride (1 drop) was added and stirring was continued for 1 h. The reaction mixture was diluted with DCM and the organic layer was washed with water, then dried (Na2SO4) and concentrated in vacuo affording (3-phenylbenzo[b]thiophen-2-yl)methyl methanesulfonate as a yellow oil (408 mg, 87%). 1H NMR (DMSO, 400 MHz): δ 8.07-8.02 (1H, m), 7.62-7.56 (2H, m), 7.55-7.37 (6H, m), 4.96 (2H, s), 3.33 (3H, s).

Workup

temperaturethe mixture was slowly warmed to RT
stirringAfter 2.5 h stirring at RT
stirringstirring
waitwas continued for 1 h
washthe organic layer was washed with water
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e9c38d725c044d07bc9fdd5885f402ec
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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