Thionyl Chloride → 1-(Chloromethyl)-2-fluoro-5-methoxy-4-nitrobenzene

HRID 1947893Notes

Reaction equation

HRID 1947893 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13]O.S(Cl)([Cl:17])=O>C(Cl)Cl>[Cl:17][CH2:13][C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67255286(2-Fluoro-5-methoxy-4-nitrophenyl)methanol2×

Product 1

HCID 672551071-(Chloromethyl)-2-fluoro-5-methoxy-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2-fluoro-5-methoxy-4-nitrophenyl)methanol (Compound 130D, 1.45 g, 7.21 mmol) in anhydrous DCM (17.0 mL) was charged with Thionyl chloride (1.055 mL, 14.5 mmol). and stirred while refluxing for 16 h. The reaction mixture was concentrated under reduced pressure to yield a brown solid. This material was used without any further purification. 1H NMR (CDCl3, 400 MHz): δ=3.99 (s, 3H), 4.65 (d, J=1.01 Hz, 2H), 7.19 (d, J=5.81 Hz, 1H), 7.65 (d, J=8.84 Hz, 1H).

Workup

  1. temperaturewhile refluxing for 16 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto yield a brown solid
  4. customThis material was used without any further purification

Sources & evidence

ORD record
ord-d946f88d850644c4aceac82c8046a2d2
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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