3-Fluoro-4-nitrobenzaldehyde → (E)-3-(3-Fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester

HRID 1690562Notes

Reaction equation

HRID 1690562 reaction equation
[Cl-].[C:2]([O:6][C:7]([CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CC(C)([O-])C.[K+].[F:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][C:43]=1[N+:44]([O-:46])=[O:45])[CH:39]=O>O1CCCC1>[C:2]([O:6][C:7](=[O:8])/[CH:9]=[CH:39]/[C:38]1[CH:41]=[CH:42][C:43]([N+:44]([O-:46])=[O:45])=[C:36]([F:35])[CH:37]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 38081203-Fluoro-4-nitrobenzaldehydeHCID 16211488(2-(tert-Butoxy)-2-oxoethyl)triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 66905416(E)-3-(3-Fluoro-4-nitro-phenyl)-acrylic acid tert-butyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (tert-butoxycarbonylmethyl)triphenylphosphonium chloride (1.6 g, 3.9 mmol; [35000-37-4]) in tetrahydrofuran (10 ml) was added potassium tert-butoxide (0.44 g, 3.9 mmol). After stirring for 15 min 3-fluoro-4-nitrobenzaldehyde (0.60 g, 3.5 mmol; [160538-51-2]) was added. After 1.5 h the suspension was poured on water, the phases were separated and the aqueous phase extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash-chromatography using a gradient of n-heptane:tert-butyl methyl ether (100:0 to 80:20) to give the title compound (804 mg, 3.01 mmol; 86%) as light brown solid. MS: m/e=194.0 [M−C4H9O+].

Workup

  1. additionwas added
  2. additionAfter 1.5 h the suspension was poured on water
  3. customthe phases were separated
  4. extractionthe aqueous phase extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash-chromatography

Sources & evidence

ORD record
ord-1842b8fe0572404eb61514a4d6062641
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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