Dichloromethane → 5-Phenyl-dibenzothiophenium 1,1-difluoro-2-(2-methyl-acryloyloxy)-ethanesulfonate

HRID 1841854Notes

Reaction equation

HRID 1841854 reaction equation
[Br-].[C:2]1([S+:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][C:22]([F:34])([S:30]([O-:33])(=[O:32])=[O:31])[CH2:23][O:24][C:25](=[O:29])[C:26]([CH3:28])=[CH2:27].C([NH+](CC)CC)C.ClCCl>O>[F:34][C:22]([F:21])([S:30]([O-:33])(=[O:32])=[O:31])[CH2:23][O:24][C:25](=[O:29])[C:26]([CH3:28])=[CH2:27].[C:2]1([S+:8]2[C:9]3[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=3[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateHCID 867124565-Phenyl-5H-dibenzo[b,d]thiophen-5-ium Bromide

Product 1

HCID 867124555-Phenyl-dibenzothiophenium 1,1-difluoro-2-(2-methyl-acryloyloxy)-ethanesulfonateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-phenyl-5H-dibenzo[b,d]thiophenium bromide (80.0 g, 234 mmol) and triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate (78.5 g, 238 mmol) were dissolved in H2O (750 mL) and dichloromethane (750 mL) and stirred at r.t. for 18 h. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×500 mL). The combined organic layers were washed with water (3×1 L) and concentrated in vacuo to afford the title compound (109 g, 95%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) δ: 8.56 (dd, J=7.5, 1 Hz, 2H), 8.42 (d, J=8 Hz, 2H), 8.05 (dt, J=8 Hz, 1 Hz, 2H), 7.77-7.87 (m, 5H), 7.69 (dt, J=8, 1 Hz, 2H), 6.14-6.16 (m, 1H), 5.66-5.69 (m, 1H), 4.75 (dd, J=15, 15 Hz, 2H), 1.93-1.94 (m, 3H).

Workup

  1. customThe dichloromethane layer was separated
  2. washthe aqueous phase washed with dichloromethane (3×500 mL)
  3. washThe combined organic layers were washed with water (3×1 L)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d6e034e84fe45a2be50377574137b79
Source dataset
uspto-grants-2015_02
Patent number
US08945814B2

Reaction notes

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