Water → 5-Fluoro-2,3-dihydro-1,4-benzodioxine

HRID 1943237Notes

Reaction equation

HRID 1943237 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18]Br.O>CN(C=O)C>[F:1][C:2]1[C:3]2[O:9][CH2:18][CH2:17][O:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 677643-Fluorocatechol

Product 1

HCID 124645225-Fluoro-2,3-dihydro-1,4-benzodioxine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-fluoro-1,2-benzenediol (5.278 g, 41.2 mmol) in DMF (50 ml) was treated with potassium carbonate (17.08 g, 124 mmol) and 1,2-dibromoethane (3.91 ml, 45.3 mmol) and stirred at rt for 72 h. The reaction was treated with water (200 ml) and extracted 3×200 ml (EtOAc). The combined organic extracts were washed with water (200 ml), brine (200 ml), dried (MgSO4), evaporated and chromatographed (0-20% EtOAc-Cyclohexane) to give product as a clear oil. (2.437 g, 38%).

Workup

  1. extractionextracted 3×200 ml (EtOAc)
  2. washThe combined organic extracts were washed with water (200 ml), brine (200 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customchromatographed (0-20% EtOAc-Cyclohexane)
  6. customto give product as a clear oil

Sources & evidence

ORD record
ord-7a812be6c45a48f08dd58e8f74d4d612
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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