Carbon tetrabromide → HCID 10264412, compound

HRID 2255576Notes

Reaction equation

HRID 2255576 reaction equation
O[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>ClCCl>[Br:35][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10442615ethyl 2-hydroxy-2-o-tolylacetate

Product 1

HCID 10264412HCID 10264412, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 0.425 g (2.19 mmol) of the product of Step B dissolved in 10 mL of dichloromethane was added 0.717 g (2.74 mmol) of triphenylphosphine followed by 0.908 g (2.74 mmol) of carbon tetrabromide. After 30 minutes the reaction was allowed to warm to room temperature and stirring was continued for 2 hours. The reaction mixture was evaporated in vacuo and the residue was purified on a silica gel flash chromatography column eluted with 5% ethyl acetate/hexane to afford 0.373 g (66%) of the title compound.

Workup

  1. waitwas continued for 2 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe residue was purified on a silica gel flash chromatography column
  4. washeluted with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2e8ba191e76744b6b2ae2ac6930e048c
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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