Thionyl Chloride → 1-Benzyloxy-4-chloromethyl-2-trifluoromethyl-benzene

HRID 19940노트

반응식

HRID 19940 반응식
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][C:14]=1[C:21]([F:24])([F:23])[F:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][Cl:3])=[CH:15][C:14]=1[C:21]([F:24])([F:23])[F:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 16749447(4-Benzyloxy-3-trifluoromethylphenyl)methanol

생성물 1

HCID 167490241-Benzyloxy-4-chloromethyl-2-trifluoromethyl-benzene

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Thionyl chloride (2.0 mL) was added to solution of (4-benzyloxy-3-trifluoromethyl-phenyl)-methanol (CAB03047, 3.10 g, 11.0 mmol) in dichloromethane (20 mL). The solution was stirred for 1 h at room temperature and concentrated under reduced pressure. Then diethyl ether (100 mL) and water (20 mL) were added. The organic layer was separated, washed with conc. sodium bicarbonate solution (10 mL), dried over sodium sulphate and concentrated under reduced pressure. The resulting oil solidified after a few minutes and was dried under high vacuum. Yield: 3.25 g (98%). 1H-NMR (400 MHz, CDCl3) δ=4.57 (s, 2H, —CH2Cl), 5.22 (s, 2H, —OCH2Ph), 7.02 (d, J=8.5 Hz, 1H), 7.31-7.52 (m, 6H), 7.63 (d, J=2.0 Hz, 1H). LRMS (FAB+): 91.1 (100), 265.2 (8), 300.1 (10, [M]+).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionThen diethyl ether (100 mL) and water (20 mL) were added
  3. customThe organic layer was separated
  4. washwashed with conc. sodium bicarbonate solution (10 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. waitThe resulting oil solidified after a few minutes
  8. customwas dried under high vacuum

출처 및 근거

ORD 기록
ord-9585e48e926c491089c838fb18e2c2bc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745472B2

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