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

HRID 242891Notes

Reaction equation

HRID 242891 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([CH3:23])[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[S:15][C:16]=1[CH2:17][OH:18].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:6]1([CH3:23])[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[S:15][C:16]=1[CH2:17][O:18][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68157058HCID 68157058, compound

Product 1

HCID 86668875(3-o-Tolylbenzo[b]thiophen-2-yl)methyl methanesulfonateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (158 μL, 2.04 mmol) was added dropwise to a solution of (3-o-tolylbenzo[b]thiophen-2-yl)methanol (432 mg, 1.70 mmol) and DIPEA (385 μL, 2.21 mmol) in anhydrous DCM (10 mL) at RT. Stirring at RT was continued for 18 h then the reaction mixture was washed with water, dried (Na2SO4) and concentrated in vacuo affording the title compound as a brown oil (424 mg, 75%). 1H NMR (DMSO-d6, 400 MHz): δ 8.05 (1H, d, J=8.04 Hz), 7.45-7.40 (3H, m), 7.38-7.32 (2H, m), 7.21 (1H, d, J=7.40 Hz), 7.12 (1H, d, J=7.98 Hz), 4.82 (1H, d, J=12.41 Hz), 4.76 (1H, d, J=12.41 Hz), 3.32 (3H, s), 1.99 (3H, s)

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7575b37f07e4b7a9574913820699f66
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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