1,4-Benzodioxane-2-methanol → 2-Bromomethyl-1,4-benzodioxane

HRID 892839Notes

Reaction equation

HRID 892839 reaction equation
O[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[Br:13]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:13][CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1

Participants

4

Reactant 2

HCID 193141,4-Benzodioxane-2-methanolHCID 70579Triphenylphosphine dibromide

Product 1

HCID 983332-Bromomethyl-1,4-benzodioxane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Hydroxymethyl-1,4-benzodioxane (17.9 g, 107 mmol) is taken up in acetonitrile (200 mL) and treated with dibromotriphenylphosphorane (50 g, 119 mmol). The mixture is stirred for 30 minutes and evaporated. The residue is taken up in a 1:1 mixture of ether/hexane, and triphenylphosphine oxide is removed by filtration. The solvent is removed by evaporation to give 2-bromomethyl-1,4-benzodioxane as a brownish solid. This material is used without further purification.

Workup

  1. customevaporated
  2. additionThe residue is taken up in a 1:1 mixture of ether/hexane, and triphenylphosphine oxide
  3. customis removed by filtration
  4. customThe solvent is removed by evaporation

Sources & evidence

ORD record
ord-d82faf2556b940ff92ec3fa301ac8dab
Source dataset
uspto-grants-1992_06
Patent number
US05120758

Reaction notes

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