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

HRID 1841854ノート

反応式

HRID 1841854 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0d6e034e84fe45a2be50377574137b79
出典データセット
uspto-grants-2015_02
特許番号
US08945814B2

反応ノート

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