Water → Ethyl 4-amino-2-(2,2,2-trifluoroethoxy)-5-nitrobenzoate

HRID 578058Notes

Reaction equation

HRID 578058 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[NH2:7][C:8]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10](F)[CH:9]=1.O>C1COCC1>[NH2:7][C:8]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 59529828Ethyl 4-amino-2-fluoro-5-nitrobenzoate

Product 1

HCID 67230732Ethyl 4-amino-2-(2,2,2-trifluoroethoxy)-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Potassium tert.-butylate (0.97 g, 8.7 mmol) was added to 2,2,2-trifluoroethanol (0.63 mL, 8.8 mmol) in 20 mL THF at ambient temperature and stirred for 10 min. Then the mixture was cooled to 5° C. and ethyl 4-amino-2-fluoro-5-nitro-benzoate (1.80 g, 7.9 mmol) in 20 mL THF was added and stirred for 1 h at 5° C. Then the mixture was poured into water, extracted with ethyl acetate, the combined organic layers dried over MgSO4 and evaporated to dryness.

Workup

  1. stirringstirred for 1 h at 5° C
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic layers dried over MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-bb633e569487447387b513dfe4076c95
Source dataset
uspto-grants-2015_05
Patent number
US09040565B2

Reaction notes

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