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

HRID 242886Notes

Reaction equation

HRID 242886 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>[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][O:18][S:2]([CH3:1])(=[O:4])=[O:3])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21931917(3-Phenylbenzo[b]thiophen-2-yl)methanol

Product 1

HCID 86668872(3-Phenylbenzo[b]thiophen-2-yl)methyl methanesulfonateYield 87%

Reagents, catalysts & solvents 2

HCID 31297Methanesulfonyl chlorideCatalystHCID 6344DichloromethaneSolvent2×

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 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 fraction washed with water, dried (Na2SO4) and concentrated in vacuo affording the title compound as a yellow oil (408 mg, 87%). 1H NMR (DMSO-d6, 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

  1. temperaturethe mixture was slowly warmed to RT
  2. waitAfter 2.5 h at RT
  3. stirringstirring
  4. waitwas continued for 1 h
  5. washthe organic fraction washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbcb0948768b44889f382e0dcfa8196d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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