Benzyl Bromide → HCID 69389165, compound

HRID 916847Notes

Reaction equation

HRID 916847 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10].C(N(C(C)C)CC)(C)C.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([O:11][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:10]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 69385356HCID 69385356, compound

Product 1

HCID 69389165HCID 69389165, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-hydroxybutyl)benzoic acid (100 mg) in dry DMF (10 ml) was treated with diisopropylethylamine (0.134 ml) and benzyl bromide (106 mg) and the reaction mixture was stirred for 65 h. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with sat. NH4Cl(aq), dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (SPE, gradient Cyclohexane to cyclohexane-EtOAc 1:1) to give the title compound LCMS RT=3.38 min.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washThe organic phase was washed with sat. NH4Cl(aq)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SPE, gradient Cyclohexane to cyclohexane-EtOAc 1:1)

Sources & evidence

ORD record
ord-a89fac26cb2a45718041ea4ae6b84558
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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