Carbon tetrabromide → HCID 67245550, compound

HRID 2238468Notes

Reaction equation

HRID 2238468 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH:11]([CH2:26]O)[CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:29]C(Br)(Br)Br>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9](=[O:28])[NH:10][CH:11]([CH2:26][Br:29])[CH2:12][CH2:13][CH2:14][N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11205Carbon tetrabromideHCID 67246530HCID 67246530, compound

Product 1

HCID 67245550HCID 67245550, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At −20° C. under N2 to the suspension of 3-2 (253 mg, 0.66 mmol) and TPP (260 mg, 1.5 equiv) in toluene is added tetrabromocarbon (242 mg, 1.1 equiv) and the reaction mixture stirred at room temperature overnight. The reaction mixture is concentrated in vacuo and the crude product purified by column chromatography eluted with hexane and EtOAc (2:1). The purified product, [1-Bromomethyl-4-phthalimido-butyl]-carbamic acid benzyl ester (3-3), is obtained as a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe crude product purified by column chromatography
  3. washeluted with hexane and EtOAc (2:1)

Sources & evidence

ORD record
ord-992bd28ff14f41d699df39c7de020cd2
Source dataset
uspto-grants-2010_05
Patent number
US07718802B2

Reaction notes

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