Water → (7-Bromo-5-chloro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol

HRID 39026Notes

Reaction equation

HRID 39026 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]([Cl:12])[C:6]=1[O:13][CH2:14][CH:15]1[CH2:17][O:16]1)(=O)C.[OH-].[K+].O>O1CCOCC1>[Br:11][C:9]1[CH:8]=[C:7]([Cl:12])[C:6]2[O:13][CH2:14][CH:15]([CH2:17][OH:16])[O:4][C:5]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 866529535-Bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl acetate

Product 1

HCID 66878380(7-Bromo-5-chloro-2,3-dihydro-1,4-benzodioxin-2-yl)methanolYield 8.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl acetate (4.4 g, 13.7 mmol) in dioxane (20 ml) was added KOH (10%, 40 ml) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. Water was added and the solution was extracted with EtOAc: The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (0.34 g). MS m/z (rel. intensity, 70 eV) 280 (M+, bp), 278 (78), 224 (68), 222 (54), 57 (37).

Workup

  1. extractionthe solution was extracted with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customPurification on flash column chromatography (isooctane/EtOAc)

Sources & evidence

ORD record
ord-c63928e4aaab43de9b674b43cc9765ef
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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