Diethyl Ether → 1-Bromo-3-cyclopropoxybenzene

HRID 2382174Notes

Reaction equation

HRID 2382174 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%.

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

Sources & evidence

ORD record
ord-439538d230f249999bc3e9d8f3384436
Source dataset
uspto-grants-2012_09
Patent number
US08258308B2

Reaction notes

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