Dimethylformamide → 1-Bromo-4-(cyclopropylmethoxy)benzene

HRID 40560

Reaction equation

HRID 40560 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH:11]1[CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 80013(Chloromethyl)cyclopropane

Product 1

HCID 156257521-Bromo-4-(cyclopropylmethoxy)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5.0 g (28.9 mmol) 4-bromophenol, 3.93 g (43.4 mmol) (chloromethyl)cyclopropane and 7.99 g (57.8 mmol) K2CO3 are added to 10 mL DMF and stirred at 80° C. over night. Afterwards the reaction mixture is diluted with water and extracted with DCM. The organic layer is dried with MgSO4 and the solvent is removed in vacuo.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer is dried with MgSO4
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2949511e5a7443a78404720baec74d54
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Linked notes

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