1,3-Dibromopropane → HCID 23590910, compound

HRID 1610934Notes

Reaction equation

HRID 1610934 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[Br:23][CH2:24][CH2:25][CH2:26]Br.C([O-])([O-])=O.[K+].[K+]>C(C(C)=O)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH3:21])([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:26][CH2:25][CH2:24][Br:23])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionate

Product 1

HCID 23590910HCID 23590910, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-(4-Hydroxyphenyl)-2-methyl-2-phenoxypropionic acid ethyl ester (4.0 g, 13.3 mmol) and 1,3-dibromopropane (7.0 mL, 66.6 mmol) are dissolved in methyl ethyl ketone (100 mL). Powdered K2CO3 (2.4 g, 17.3 mmol) is added. The mixture is heated under reflux for 4 h, cooled, filtered and concentrated to an oil. The crude oil is chromatographed (silica gel; hexane/EtOAc, 5:1 to 1:4) to afford the title compound (5.0 g, 89%). MS (ESI) m/z 421 (M+H)+. Step 2.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customThe crude oil is chromatographed (silica gel; hexane/EtOAc, 5:1 to 1:4)

Sources & evidence

ORD record
ord-7411424e50864e219873b5b5fa4b5e94
Source dataset
uspto-grants-2006_01
Patent number
US06984661B2

Reaction notes

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