Carbon tetrabromide → HCID 19385600, compound

HRID 2399488Notes

Reaction equation

HRID 2399488 reaction equation
[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][C:10]=1[Cl:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Br:19])=[CH:11][C:10]=1[Cl:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54570390(4-{[tert-Butyl(dimethyl)silyl]oxy}-3-chlorophenyl)methanol

Product 1

HCID 19385600HCID 19385600, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (0° C.) solution of 4.00 g (14.1 mmol) of the product of Step B dissolved in 70 mL of CH2Cl2 was added 5.84 g (17.6 mmol) of carbon tetrabromide and 4.61 g (17.6 mmol) of triphenylphosphine. After the addition the reaction mixture was allowed to warm to room temperature and was stirred 3 hours. The mixture was then evaporated in vacuo and purified on a silica gel flash chromatography column eluted with 2% ethyl acetate/hexane to afford 4.50 g (92%) of the title compound.

Workup

  1. additionAfter the addition the reaction mixture
  2. stirringwas stirred 3 hours
  3. customThe mixture was then evaporated in vacuo
  4. custompurified on a silica gel flash chromatography column
  5. washeluted with 2% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8aebb875bb4540b09beb3b6316fcc6a4
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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