Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 72459876, compound

HRID 1295801Notes

Reaction equation

HRID 1295801 reaction equation
[Br:1][C:2]1[C:7]([CH:8]=O)=[C:6]([F:10])[C:5]([N:11]=[N:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:4]([F:18])[CH:3]=1.C1(P(=[CH:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:42]([O:41][C:39](=[O:40])[CH:38]=[CH:8][C:7]1[C:2]([Br:1])=[CH:3][C:4]([F:18])=[C:5]([N:11]=[N:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:6]=1[F:10])[CH3:43]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 58911255HCID 58911255, compound

Product 1

HCID 72459876HCID 72459876, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 0.3 1 three necked flask fitted with a magnetical stirrer and dropping funnel under inert atmosphere, 6.62 g (20.8 mmol, 1 eq) of 6-bromo-2,4-difluoro-3-(pyrrolidin-1-ylazo)-benzaldehyde a9 are dissolved in THF (100 ml) and cooled down to 0° C. Ethyl (triphenylphosphoranylidene)acetate (9.43 g, 1.3 eq) is then added under efficient stirring, the temperature raising to 10° C. The mixture is kept under stirring one hour at 0° C., and then overnight at room temperature. The mixture is concentrated to dryness, the residue suspended in diethyl ether, the triphenylphospine oxide is filtered off and the filtrate concentrated to dryness. The residue is purified by PrepLC on silicagel (CH2Cl2/pentane: 50/50 (v/v)) to give 4.17 g of pure of 3-[6-bromo-2,4-difluoro-3-(pyrrolidin-1-ylazo)-phenyl]-acrylic acid ethyl ester a10 (47%).

Workup

  1. customIn a 0.3 1 three necked flask fitted with a magnetical stirrer
  2. temperaturethe temperature raising to 10° C
  3. customovernight
  4. customat room temperature
  5. concentrationThe mixture is concentrated to dryness
  6. filtrationthe triphenylphospine oxide is filtered off
  7. concentrationthe filtrate concentrated to dryness
  8. customThe residue is purified by PrepLC on silicagel (CH2Cl2/pentane: 50/50 (v/v))

Sources & evidence

ORD record
ord-a4dc5dbd20f74da79a0a3b9491f6a4f2
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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