Phenethyl bromide → HCID 86725632, compound

HRID 878676Notes

Reaction equation

HRID 878676 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-d069f62c3ae84332b78d11b86f4ac22b
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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