2-Nitroanisole → Methyl alpha-chloro-3-methoxy-4-nitrophenylacetate

HRID 1018011Notes

Reaction equation

HRID 1018011 reaction equation
CC(C)([O-])C.[K+].[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])([O-:9])=[O:8].[Cl:18][CH:19](Cl)[C:20]([O:22][CH3:23])=[O:21]>C(O)(=O)C>[Cl:18][CH:19]([C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[C:11]([O:16][CH3:17])[CH:12]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 70482-NitroanisoleHCID 8315Methyl dichloroacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10061131Methyl alpha-chloro-3-methoxy-4-nitrophenylacetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of potassium t-butoxide (1.44 kg) in dimethylformamide(6.61) cooled to −5° C. to −10° C., was treated with a mixture of 2-nitroanisole (690 g) and methyl dichloroacetate (915 g) over 4 hours, whilst maintaining the temperature below −5° C. The reaction mixture was then treated with acetic acid (770 ml) and then with water (6.61) and then e extracted three times with tert-butyl methyl ether (5.51). The combined extracts were washed with water (5.51), then with saturated sodium bicarbonate solution (5.51), then with saturated brine (5.51) and then dried over magnesium sulphate to give a solution of methyl α-chloro-3-methoxy-4-nitrophenylacetate.

Workup

  1. temperaturecooled to −5° C. to −10° C.
  2. temperaturewhilst maintaining the temperature below −5° C
  3. extractionwith water (6.61) and then e extracted three times with tert-butyl methyl ether (5.51)
  4. washThe combined extracts were washed with water (5.51)
  5. dry with materialwith saturated sodium bicarbonate solution (5.51), then with saturated brine (5.51) and then dried over magnesium sulphate

Sources & evidence

ORD record
ord-4c4a2c05aa8c49e4a858341b89cd98bd
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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