Heptane → Triphenylphosphine Oxide

HRID 2242351Notes

Reaction equation

HRID 2242351 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C1C=CC(OC)=C(C[OH:31])C=1)(C)(C)C.C(Br)(Br)(Br)Br.CCCCCCC>C(Cl)Cl>[C:14]1([P:7](=[O:31])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8900HeptaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20777166HCID 20777166, compound

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

Triphenyl phosphine (5.84 g, 22.3 mmol) was added to a solution of (5-tert-butyl-2-methoxyphenyl)methanol (4.20 g, 21.8 mmol) in anhydrous DCM (80 ml) and the mixture cooled to 10° C. Carbon tetrabromide (7.39 g, 22.3 mmol) was added with stirring over 10 min, and after 30 min the temperature was raised to ambient temperature. Stirring continued for 17.5 h when the solvent was lowered to 20 ml under reduced pressure. Addition of heptane (80 ml) with stirring resulted in precipitation of triphenyl phosphine oxide, which was removed by filtration of the mixture through dicalite. Evaporation of the filtrate gave a straw coloured gum, purification of which was achieved by chromatography on silica using heptane:DCM (1:1) as eluent to afford 2-bromomethyl-4-tert-butyl-1-methoxybenzene as a clear gum (2.02 g, 36%).

Workup

  1. temperatureafter 30 min the temperature was raised to ambient temperature
  2. stirringStirring
  3. waitcontinued for 17.5 h
  4. stirringwith stirring

Sources & evidence

ORD record
ord-c023fdd902a34e1da5d2aedd6f780d99
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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