Water → (7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 1815503Notes

Reaction equation

HRID 1815503 reaction equation
[Br:1][C:2]1[CH:9]=[C:6](C=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.C([O-])([O-])=[O:17].[K+].[K+].O>CN(C=O)C>[OH:17][CH2:14][CH:13]1[CH2:11][O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[O:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 233965(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanolYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 5-bromosalicylaldehyde (5.0 g, 24.9 mmol), and epichlorohydrin (5.6 mL, 72.1 mmol) in 20 mL of DMF at 80° C. was added K2CO3 slowly in portions. The resulting mixture was then heated at 90° C. for 3 hours. Reaction was then stopped, water was added, extracted with diethyl ether. The organic extracts were washed with water, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes to give 2.82 g (44%) of the title compound as a colorless oil.

Workup

  1. customReaction
  2. extractionextracted with diethyl ether
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a SiO2 flash column chromatography
  7. washeluting with 15-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-4c70c2fca12d4d3d8659133d30b69eef
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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