1-Bromo-3-chloropropane → HCID 22168537, compound

HRID 221813Notes

Reaction equation

HRID 221813 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22]>CC(C)=O>[Cl:22][CH2:21][CH2:20][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 22168537HCID 22168537, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-hydroxyphenylacetone (4.5 g, 30 mmol) and potassium carbonate (4.14 g, 3.0 eq.) in 50 mL of acetone was stirred under N2 as 1-bromo-3-chloro-propane was added dropwise. The reaction was heated to 80° C. overnight. The mixture was then filtered through celite, washed with acetone and concentrated to afford 1-[4-(3-chloro-propoxy)phenyl]propan-2-one (6.3 g, 93% yield): MS m/z 227 (M+H).

Workup

  1. additionwas added dropwise
  2. filtrationThe mixture was then filtered through celite
  3. washwashed with acetone
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ee5bba70497746f5afacce827cbc495e
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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