Phenethyl bromide → HCID 86725632, compound

HRID 514520Notes

Reaction equation

HRID 514520 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.Br[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([O:8][CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[CH:7]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 3271485-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 86725632HCID 86725632, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Charged 5-chloro-2-(hydroxymethyl)phenol (787 mg, 4.96 mmol), (bromoethyl)benzene (1.01 g, 5.46 mmol), K2CO3 (1.37 g, 9.93 mmol) and DMF (8 mL) to a flask, heated to 100° C. overnight. Poured into ice water, and extracted with ethyl acetate twice, and washed the organic phase with water twice, brine and dried with anhydrous Na2SO4. Solvent was then removed and purified by flash column chromatograph to give 1.0 g of the title compound (77%).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washwashed the organic phase with water twice
  3. dry with materialbrine and dried with anhydrous Na2SO4
  4. customSolvent was then removed
  5. custompurified by flash column chromatograph

Sources & evidence

ORD record
ord-37031508761f40dda32b03ab7e8c2c23
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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