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

HRID 458996Notes

Reaction equation

HRID 458996 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.C([O-])(O)=O.[Na+]>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

6

Reactant 4

HCID 7841Allyl bromideHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 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 NaHCO3 was 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. washThe aqueous solution was washed with EtOAc (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by medium pressure chromatography (9:1 hexanes:EtOAc)
  8. customprovided

Sources & evidence

ORD record
ord-56bfb42619c34c9991e2ed7d27ab4eb9
Source dataset
uspto-grants-2007_03
Patent number
US07192979B2

Reaction notes

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