Water → Methyl 4-chloro-3-methoxy-5-nitrobenzoate

HRID 62754Notes

Reaction equation

O[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16].C(Cl)(=O)C([Cl:20])=O.O>CN(C=O)C>[Cl:20][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of methyl 4-hydroxy-3-methoxy-5-nitrobenzoate (2) (4.4 g, 19 mmol) in DMF (30 mL) at 0° C. was treated with oxalyl chloride (5.09 mL, 58.1 mmol) dropwise. The mixture was then stirred at 80° C. for 3 h under a CaCl2 drying tube. The mixture was allowed to cool to RT, poured in to iced water (100 mL) and stirred for 15 min. The precipitate was collected by filtration and washed with water and MeOH to afford methyl 4-chloro-3-methoxy-5-nitrobenzoate (3) (3.2 g, 65% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ: 8.04 (1H, d), 7.77 (1H, d), 4.04 (3H, s), 3.97 (3H, s).

Workup

temperatureto cool to RT
stirringstirred for 15 min
filtrationThe precipitate was collected by filtration
washwashed with water and MeOH

Sources & evidence

ORD record: ord-21e65c90f3d64840828314bc29c0f638
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

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