Allyl bromide → Methyl 4-(3-bromopropyl)benzoate

HRID 352607Notes

Reaction equation

HRID 352607 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12]O)=[CH:6][CH:5]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C([Br:30])C=C>CC#N>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][Br:30])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 682631,1'-CarbonyldiimidazoleHCID 14425137Methyl 4-(3-hydroxypropyl)benzoate

Product 1

HCID 10801120Methyl 4-(3-bromopropyl)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(3-hydroxy-propyl)-benzoic acid methyl ester (11.98 g) and 1,1′-carbonyldiimidazole (9.0 g, 55.50 mmol) in CH3CN (200 mL) was stirred at room temperature for 1.5 h. Allyl bromide (20 mL) was added and the reaction mixture was heated under reflux for 20 h. The reaction mixture was cooled to room temperature and saturated aqueous NaHCO3was added. The aqueous solution was washed with EtOAc (3×) and the organic solutions were combined, dried (MgSO4), filtered and concentrated. Purification by medium pressure chromatography (9:1 hexanes:EtOAc) provided the title compound of Preparation 4.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 20 h
  3. additionsaturated aqueous NaHCO3was added
  4. washThe aqueous solution was washed with EtOAc (3×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by medium pressure chromatography (9:1 hexanes:EtOAc)
  9. customprovided

Sources & evidence

ORD record
ord-5b30b649f6b44b599e105f5a025099ed
Source dataset
uspto-grants-2004_06
Patent number
US06747054B2

Reaction notes

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