Pyridine → 4-(4-Fluorophenoxy)benzylchloride

HRID 474604Notes

Reaction equation

HRID 474604 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:25])=O>ClCCl>[Cl:25][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 22293127[4-(4-Fluorophenoxy)phenyl]methanol

Product 1

HCID 222931364-(4-Fluorophenoxy)benzylchlorideYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of (4-(4-fluorophenoxy)phenyl)methanol (7 g, 32.1 mmol) and pyridine (5.19 mL, 64.2 mmol) in dichloromethane (DCM) (100 mL) was added sulfurous dichloride (7.63 g, 64.2 mmol) dropwise at 0° C. After addition the mixture was stirred at room temperature overnight. The mixture was washed with saturated NaHCO3 solution (40 mL×2) and brine (40 mL), the organic phase was dried over Na2SO4, filtered and concentrated to leave the crude product, which was purified by column chromatography (silica-gel, elution with PE: EtOAc=6:1) to afford the pure 1-(chloromethyl)-4-(4-fluorophenoxy)benzene (2.2 g, 8.83 mmol, 27.5% yield) as light yellow oil. LCMS: rt=1.56 min, [M+H+]=237

Workup

  1. additionAfter addition the mixture
  2. washThe mixture was washed with saturated NaHCO3 solution (40 mL×2) and brine (40 mL)
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave the crude product, which
  7. customwas purified by column chromatography (silica-gel, elution with PE: EtOAc=6:1)

Sources & evidence

ORD record
ord-88164b63b85c47d097e27997ef1ae453
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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