Boron tribromide → 2,3-Dihydro-1,4-benzodioxin-5-ol

HRID 865938

Reaction equation

HRID 865938 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:16]2[O:15][CH2:14][CH2:13][O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[C:16]2[O:15][CH2:14][CH2:13][O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 743712,3-Dihydro-5-methoxy-1,4-benzodioxin

Product 1

HCID 825202,3-Dihydro-1,4-benzodioxin-5-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., boron tribromide (5.6 cm3) is added slowly to a solution of 5-methoxy-1,4-benzodioxane (5 g, 30.1 mmol) in 25 cm3 of CH2Cl2. The mixture is stirred at 0° C. for 15 min, the solution is then hydrolysed with 10 cm3 of water and the product is extracted with CH2Cl2. Purification on a silica column (eluent: 100% CH2Cl2) enables 4.49 g of a colorless oil to be obtained.

Workup

  1. extractionhydrolysed with 10 cm3 of water and the product is extracted with CH2Cl2
  2. customPurification on a silica column (eluent: 100% CH2Cl2)
  3. customto be obtained

Sources & evidence

ORD record
ord-ce06de15ee3d4369a4a6f27e4b83b51b
Source dataset
uspto-grants-1996_10
Patent number
US05569669

Linked notes

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