Water → HCID 86721081, compound

HRID 930940Notes

Reaction equation

HRID 930940 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.Br[CH2:11][CH:12]1[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][CH:12]2[CH2:14][CH2:13]2)=[C:4]([I:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 109245324-Bromo-2-iodophenol

Product 1

HCID 86721081HCID 86721081, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromo-2-iodophenol (5.00 g, 16.7 mmol), bromomethylcyclopropane (2.26 g, 16.7 mmol) and cesium carbonate (6.54 g, 20.1 mmol) in 15 mL dimethylformamide was stirred at 50° C. overnight. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with water, saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated to the provide title compound (5.84 g, 99% yield).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water, saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated to the

Sources & evidence

ORD record
ord-0b9c25748da6477bb08233fa87615fb8
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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