Methanesulfonyl chloride → HCID 86668871, compound

HRID 242885Notes

Reaction equation

HRID 242885 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[CH2:21][OH:22])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:6]1([C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[CH2:21][O:22][S:2]([CH3:1])(=[O:4])=[O:3])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 81531Diisopropylethylamine2×HCID 68157997HCID 68157997, compound

Product 1

HCID 86668871HCID 86668871, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (160 μL, 2.05 mmol) was added dropwise to a solution of (3-phenylbenzofuran-2-yl)methanol (367 mg, 1.64 mmol) and DIPEA (343 μL, 1.97 mmol) in anhydrous DCM (10 mL) at 0° C. Stirring at 0° C. was continued for 15 min, then the mixture slowly warmed to RT. After 2 h at RT, additional amounts of methanesulfonyl chloride (80 μL, 1.03 mmol) and DIPEA (172 μL, 0.99 mmol) were added and stirring continued for 1.5 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 an oil (443 mg, 89%). 1H NMR (DMSO-d6, 400 MHz): δ 7.71-7.64 (2H, m), 7.62-7.56 (4H, m), 7.52-7.41 (2H, m), 7.37-7.32 (1H, m), 4.98 (2H, s), 3.89 (3H, s)

Workup

  1. temperaturethe mixture slowly warmed to RT
  2. waitAfter 2 h at RT
  3. stirringstirring
  4. waitcontinued for 1.5 h
  5. washthe organic fraction washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8d27648f34a4c20946f0350ec1f9785
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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