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

HRID 1841854노트

반응식

HRID 1841854 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0d6e034e84fe45a2be50377574137b79
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08945814B2

반응 노트

불러오는 중…