Dimethyl Sulfide → 2-Hydroxyphenyl methanesulfonate

HRID 2239576ノート

反応式

HRID 2239576 の反応式
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12]CC1C=CC=CC=1)(=[O:4])=[O:3].B(F)(F)F.CCOCC.CSC>C(Cl)Cl>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 866258732-(Benzyloxy)phenyl methanesulfonate

生成物 1

HCID 132483392-Hydroxyphenyl methanesulfonate収率 92.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(Benzyloxy)phenyl methanesulfonate (4.00 g, 14.37 mmol) was dissolved in dry DCM (50 mL) under nitrogen atmosphere. Boron trifluoride diethyl etherate (8.16 g, 57.49 mmol) was added followed by dimethyl sulfide (3.57 g, 57.49 mmol) and the reaction mixture was stirred at rt overnight. The reaction mixture was poured onto ice and the aqueous layer was extracted with DCM. The organic layers were combined, washed with water, dried (Na2SO4), filtered and evaporated to give the title compound (2.49 g, 92%). 1H NMR (500 MHz, CDCl3): δ 3.26 (s, 3H), 6.16 (s, 1H), 6.96 (dt, 1H), 7.09 (dd, 1M), 7.22-7.28 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 37.74, 119.01, 121.65, 123.71, 129.09, 136.99, 148.43; Mass Spectrum: M−H+ 187.

後処理

  1. additionThe reaction mixture was poured onto ice
  2. extractionthe aqueous layer was extracted with DCM
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-2ecf98af6e764a3ea094832299cdff4f
出典データセット
uspto-grants-2010_05
特許番号
US07723333B2

反応ノート

読み込み中…