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

HRID 901175ノート

反応式

HRID 901175 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-4c696f1b2d324baabb580df456a98ab8
出典データセット
uspto-grants-2008_04
特許番号
US07361677B2

反応ノート

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