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

HRID 901165Notes

Reaction equation

HRID 901165 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[F:21])[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[F:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21976875(4-(Benzyloxy)-3-fluorophenyl)methanol

Product 1

HCID 110540901-Benzyloxy-4-chloromethyl-2-fluoro-benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (5 mL) was added to solution of (4-benzyloxy-3-fluoro-phenyl)-methanol (CAB03017, 6.80 g, 29.28 mmol) in dichloromethane (50 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 residue was dissolved in dichloromethane (5 mL) and precipitated by addition of hexane (ca. 50 mL). The precipitate was filtered off and dried under high vacuum. Yield: 7.01 g (95%) white powder. 1H-NMR (400 MHz, CDCl3) δ=4.52 (s, 2H, —CH2Cl), 5.15 (s, 2H), 6.96 (dd, J=8.2, 8.2 Hz, 1H), 7.04-7.06 (m, 1H), 7.15 (dd, J=11.7, 2.4 Hz, 1H), 7.31-7.45 (m.5H). LRMS (FAB+): 91 (100), 215.0 (10), 250.0 (16, [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. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  8. customprecipitated by addition of hexane (ca. 50 mL)
  9. filtrationThe precipitate was filtered off
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-637b9c34c46d4ab08591e6f464ddc5bc
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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