Carbon tetrabromide → 5-Bromomethyl-2-phenyl-1,3-dioxane

HRID 728484Notes

Reaction equation

HRID 728484 reaction equation
O[CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1.[Br:15]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[Br:15][CH2:2][CH:3]1[CH2:8][O:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10679342(2-Phenyl-1,3-dioxan-5-yl)methanol

Product 1

HCID 148351015-Bromomethyl-2-phenyl-1,3-dioxaneYield 75.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

To a vigorously stirred solution of 19.4 g (0.1M) of 5-hydroxymethyl-2-phenyl-1,3-dioxane m1 and 33.1 g (0.1M) of tetrabromomethane in 60 ml of anhydrous benzene at 70° C., is added 26.2 g (0.1M) of triphenylphosphine in 45 minutes. After stirring at 70° C. for an another 30 minutes, the solvent is evaporated. To the residue is added 200 ml of ether and ether insoluble triphenylphosphine oxide is removed by filtration. After repeating this procedure twice, the solvent of the filtrated is evaporated. Distillation of the residual product gives 19.391 g (75.4% yield) of the titled compound m2.

Workup

  1. customthe solvent is evaporated
  2. additionTo the residue is added 200 ml of ether and ether insoluble triphenylphosphine oxide
  3. customis removed by filtration
  4. customthe solvent of the filtrated is evaporated
  5. distillationDistillation of the residual product

Sources & evidence

ORD record
ord-50f0085ed74e4105b55f2c80870ee582
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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