Dimethyl Sulfide → 2-Hydroxyphenyl methanesulfonate

HRID 2239576노트

반응식

HRID 2239576 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 132483392-Hydroxyphenyl methanesulfonate수율 92.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ecf98af6e764a3ea094832299cdff4f
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723333B2

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