Carbon tetrabromide → HCID 23064812, compound

HRID 735403Notes

Reaction equation

HRID 735403 reaction equation
Br[C:2]([Br:5])(Br)Br.[CH:6]12[O:14][CH:9]([CH:10](CO)[CH2:11]1)[CH:8]=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH:9]12[O:14][CH:6]([CH:11]([CH2:2][Br:5])[CH2:10]1)[CH:7]=[CH:8]2

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2650927-oxabicyclo[2.2.1]hept-5-en-2-ylmethanol

Product 1

HCID 23064812HCID 23064812, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Tetrabromomethane (1.161 g, 3.50 mmol) was added to a solution of 7-oxanorborn-2-en-5-ylmethanol (0.305 g, 2.50 mmol, from Example 2) in CH2Cl2 (12.5 ml). The solution was cooled to 0° C. and admixed with triphenylphosphine (1.836 g, 7 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 12 h. The solvent was removed under reduced pressure and the remaining solid was taken up in cyclohexane. The crude product was purified by flash chromatography (using a 98:2 mixture of cyclohexane and ethyl acetate). 0.3 g (59% of theory) of the pure product were obtained. The product was stored under cool conditions with the exclusion of light.

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was removed under reduced pressure
  3. customThe crude product was purified by flash chromatography (
  4. additiona 98:2 mixture of cyclohexane and ethyl acetate)
  5. custom0.3 g (59% of theory) of the pure product were obtained

Sources & evidence

ORD record
ord-afc0d1d530544a1a8b3b9d59f999295f
Source dataset
uspto-grants-2009_09
Patent number
US07592498B2

Reaction notes

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