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

HRID 901175Notes

Reaction equation

HRID 901175 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+).

Workup

  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

Sources & evidence

ORD record
ord-4c696f1b2d324baabb580df456a98ab8
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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