Diethyl Ether → 1-Bromo-3-cyclopropoxybenzene

HRID 2362832Notes

Reaction equation

HRID 2362832 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](=O)([O-])[O-].[K+].[K+].C(O[CH2:18][CH3:19])C>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:19]2[CH2:18][CH2:9]2)[CH:3]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 574169511-Bromo-3-cyclopropoxybenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-bromophenol (2.4 g, 13.9 mmol), bomocyclopropane (6.66 ml, 83 mmol) and potassium carbonate (9.6 g, 69.5 mmol) in DMF (16 ml) was heated at 180° C. in a microwave oven for 8 hours. The reaction mixture was diluted with a mixture of diethylether and water. The organic layer was separated, washed with water, brine, dried over Na2SO4, filtered and evaporated. An oil was obtained, 2.87 g, with a purity of 81%. This intermediate was used for the next reaction.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customAn oil was obtained
  7. customThis intermediate was used for the next reaction

Sources & evidence

ORD record
ord-ae33d090373741d88161ae3b22ce8a6f
Source dataset
uspto-grants-2014_04
Patent number
US08691852B2

Reaction notes

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