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

HRID 511325Notes

Reaction equation

HRID 511325 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, 3 H), 4.65 (d, J=1.01 Hz, 2 H), 7.19 (d, J=5.81 Hz, 1 H), 7.65 (d, J=8.84 Hz, 1 H).

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-7af9f6066d9d42cbaa7fb23b0becad1a
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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