Sodium Bicarbonate → HCID 59557741, compound

HRID 2038478Notes

Reaction equation

HRID 2038478 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH:16]=1)[CH2:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.[C:18]([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:17])=[C:6]([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[CH2:18])=[CH:10][CH:9]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59557754HCID 59557754, compound

Product 1

HCID 59557741HCID 59557741, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of Ph3PCH3I (0.97 g) in toluene (5 mL), KN(TMS)2 (0.5M in toluene, 4.8 mL) was added dropwise at room temperature. After 10 min, the solution of 4-(5-bromo-2-chlorobenzyl)benzaldehyde (intermediate AL) (0.62 g) in toluene (2 mL) was added dropwise. After 2 h, aqueous NaHCO3 was added to quench the reaction, and the resulting mixture was extracted with ethyl acetate. The organic layers were combined, washed with brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the product was purified by column chromatography to obtain pure intermediate AM (0.5 g).

Workup

  1. waitAfter 2 h
  2. customto quench
  3. customthe reaction
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated under reduced pressure
  8. customthe product was purified by column chromatography
  9. customto obtain pure intermediate

Sources & evidence

ORD record
ord-fc11bfeb9fac49d1812034dd9905e9f7
Source dataset
uspto-grants-2013_11
Patent number
US08575321B2

Reaction notes

Loading…