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

HRID 216094Notes

Reaction equation

HRID 216094 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-de9a993086e94cb7adb6ce6b2d9e4513
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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