Carbon tetrabromide → HCID 11057705, compound

HRID 843730Notes

Reaction equation

HRID 843730 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Si:25]([N:32]1[C@H:35]([CH:36]=O)[CH2:34][C:33]1=[O:38])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].C([O-])(O)=O.[Na+]>ClCCl>[Si:25]([N:32]1[C@H:35]([CH:36]=[C:1]([Br:5])[Br:2])[CH2:34][C:33]1=[O:38])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 10899970HCID 10899970, compound

Product 1

HCID 11057705HCID 11057705, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of CBr4 (3.11 g) in dichloromethane (15 ml) was added dropwise a solution of triphenylphosphine (4.92 g) in dichloromethane (15 ml) at 0° C. After stirring for 10 minutes a solution of (S)-N-tert-butyldimethylsilyl-4-formyl-2-azetidinone (1.0 g) in dichloromethane (10 ml) was added dropwise at 0° C. and stirred for 20 minutes. The mixture was poured into saturated aqueous NaHCO3 solution and extracted with dichloromethane. The extract was washed with water, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with (diethyl ether:n-hexane=1:5) to give (S)-N-tert-butyldimethylsilyl-4-(2,2dibromoethenyl)-2-azetidinone (0.83 g) as a pale yellow oil.

Workup

  1. additionwas added dropwise at 0° C.
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel eluting with (diethyl ether:n-hexane=1:5)

Sources & evidence

ORD record
ord-565832f94c0d418284f88b631adff998
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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