Hydrogen Bromide → 2-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-ol

HRID 225145Notes

Reaction equation

HRID 225145 reaction equation
[Br:1][CH2:2][C:3]([CH:5]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)=[O:4].[BH4-].[Na+].Br>CO>[O:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6][CH:5]1[CH:3]([OH:4])[CH2:2][Br:1]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 4311764Sodium borohydrideHCID 126085852-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-one

Product 1

HCID 126085902-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-olYield 25.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-70 °C

Procedure

2-Bromoacetyl-1,4-benzodioxan(53.8 g) in methanol (500 mls) was cooled to -70° C. Sodium borohydride (10.3 g) was added and the solution stirred at -70° C. for 12 hours. The solution was treated with hydrobromic acid until acidic and the solvent evaporated. The residue was dissolved in ether and the ether extracts were washed with sodium bicarbonate solution; then water and dried (MgSO4) and evaporated to give a white solid. This was recrystallised eight times from petroleum spirit 60-80 to give 14 grams of the title compound.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ether
  3. washthe ether extracts were washed with sodium bicarbonate solution
  4. dry with materialthen water and dried (MgSO4)
  5. customevaporated
  6. customto give a white solid
  7. customThis was recrystallised eight times from petroleum spirit 60-80

Sources & evidence

ORD record
ord-49ade3456d8649a7ba63b43f907aac16
Source dataset
uspto-grants-1980_11
Patent number
US04235915

Reaction notes

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