Water → 2-Fluoro-1-methoxy-4-(2-nitro-vinyl)benzene

HRID 2110618Notes

Reaction equation

HRID 2110618 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[N+:12]([CH3:15])([O-:14])=[O:13].C([O-])(=O)C.[NH4+].O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:15][N+:12]([O-:14])=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 676963-Fluoro-p-anisaldehyde2×HCID 517165Ammonium Acetate

Product 1

HCID 534146392-Fluoro-1-methoxy-4-(2-nitro-vinyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-fluoro-4-methoxybenzaldehyde [5.05 g, Intermediate (1)], nitromethane (5.3 mL) and ammonium acetate (6.3 g) in glacial acetic acid (60 mL) is heated at 110° C. for 16 hours, allowed to cool and poured into water (300 mL). The aqueous solution is extracted twice with EtOAc (200 mL). The combined extracts are washed with sodium bicarbonate solution (10%), with water, dried over sodium sulfate and evaporated affording 2-fluoro-1-methoxy-4-(2-nitro-vinyl)benzene [4.2 g, Intermediate (2)]. MS: 198 (M+H); 1H NMR (CDCl3): δ 7.9 (1H, d, J=10 Hz); 7.5 (1H, d, 10 Hz); 7.3 (2H, m); 6.95-7.15 (1H, m); 4 (3H, s).

Workup

  1. temperatureto cool
  2. extractionThe aqueous solution is extracted twice with EtOAc (200 mL)
  3. washThe combined extracts are washed with sodium bicarbonate solution (10%), with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c3cef04c97e1492ba8557b0bb7e5f361
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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