Water → Ethyl 3-(2-chloro-4-fluoro-5-nitrophenyl)-2-propenoate

HRID 1940483Notes

Reaction equation

HRID 1940483 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[CH:4]=O.[Br-].[C:15]([CH2:20][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C.O>C1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[CH:4]=[CH:20][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 73731(Ethoxycarbonylmethyl)triphenylphosphonium bromideHCID 135637752-Chloro-4-fluoro-5-nitrobenzaldehyde

Product 1

HCID 54527423Ethyl 3-(2-chloro-4-fluoro-5-nitrophenyl)-2-propenoateYield 60.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of the compound of Step C, Example 2, (11.5 gm, 56.51 mmol), (carbethoxymethyl)triphenylphosphonium bromide (24.2 gm, 56.51 mmol) and triethylamine (50 mL) in benzene (200 mL), under N2, was heated to reflux for 1 hour. Water (200 mL) and ethyl acetate (200 mL) were added. The organic layer was separated, dried over magnesium sulfate and evaporated under reduce pressure to dryness. The residue was chromatographed on silica gel using hexane:EtOAc (15:5) mixture as eluent. The fractions were combined and evaporated under reduce pressure to obtain the title compound of Step D (9.3 gm, 60%) as a yellow solid; m.p. 86°-88° C.,

Workup

  1. temperatureunder N2, was heated
  2. temperatureto reflux for 1 hour
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. customevaporated

Sources & evidence

ORD record
ord-b5c56af113654a1082ea3463ce1d1e0a
Source dataset
uspto-grants-1997_12
Patent number
US05700761

Reaction notes

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