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

HRID 2279704Notes

Reaction equation

HRID 2279704 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12]O)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].S(Cl)([Cl:16])=O>>[Cl:16][CH2:12][C:5]1[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 6029613-Methoxy-4-nitrobenzyl alcohol

Product 1

HCID 220516194-(Chloromethyl)-2-methoxy-1-nitrobenzeneYield 100%

Procedure

A mixture of (3-methoxy-4-nitrophenyl)methanol (0.5 g, 2.73 mmol) and thionyl chloride (0.3 mL, 4.09 mmol) was heated at reflux for 12 h. The reaction mixture was concentrated under reduced pressure to afford the title compound as a tan solid, 0.55 g (100% yield). This material was used in successive reactions without further purification. 1H NMR (CD3OD, 400 MHz): δ 4.00 (s, 3H), 4.60 (s, 2H), 7.05 (dd, J=8.3, 1.8 Hz, 1H), 7.14 (d, J=1.5 Hz, 1H), 7.86 (d, J=8.3 Hz, 1H). MS (ESI): m/z 202.03 [M+H]+ (UPLC-TOF: polar—3 min).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-770dc312b58c4dd4b3b404f9c39e1eef
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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