Pyridine → 4-(4-Fluorophenoxy)benzylchloride

HRID 705846Notes

Reaction equation

HRID 705846 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 22293127HCID 22293127, compound

Product 1

HCID 222931364-(4-Fluorophenoxy)benzylchlorideYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of (4-(4-fluorophenoxyl)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-fluorophenoxyl)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-72afd888eef6477c8817fbeff83dee45
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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