Water → 1-Bromo-3-cyclopropoxybenzene

HRID 42009Notes

Reaction equation

HRID 42009 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH:10]1[CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:10]2[CH2:12][CH2:11]2)[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 78037Bromocyclopropane

Product 1

HCID 574169511-Bromo-3-cyclopropoxybenzeneYield 83.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-bromophenol (4.80 mmol, 0.83 g), bromocyclopropane (27.71 mmol, 2.22 ml), K2CO3 (23.15 mmol, 3.2 g) in DMF (18 ml) was heated at 180° C. for 8 hours in a microwave oven. Water and diethyl ether were added and the organic phase was evaporated affording 0.85 g of the expected product.

Workup

  1. customthe organic phase was evaporated

Sources & evidence

ORD record
ord-34589bfa5226443b9088b777e4c58fe9
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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