Thionyl Chloride → 4-(Chloromethyl)-1-fluoro-2-methoxybenzene

HRID 1965363Notes

Reaction equation

HRID 1965363 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[O:10][CH3:11].S(Cl)([Cl:14])=O>ClCCl.CN(C)C=O>[Cl:14][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:10][CH3:11])[CH:4]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 593590(4-Fluoro-3-methoxyphenyl)methanol

Product 1

HCID 179642394-(Chloromethyl)-1-fluoro-2-methoxybenzeneYield 72.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-fluoro-3-methoxyphenyl)methanol (Claudi, et al., J. Med. Chem. 1990, 33(9):2408) (0.90 g, 5.76 mmol) in anhydrous dichloromethane (10 mL) was added thionyl chloride (0.84 mL, 12 mmol) and anhydrous N,N-dimethylformamide (2 drops). The reaction mixture was stirred at ambient temperature for 16 h and concentrated in vacuo to afford 4-(chloromethyl)-1-fluoro-2-methoxybenzene (0.73 g, 72%) as a brown oil: 1H NMR (300 MHz, CDCl3) δ 7.05-6.86 (m, 3H), 4.53 (s, 2H), 3.88 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-569e166e9225445998894117fee5b247
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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