Carbon tetrabromide → HCID 67245550, compound

HRID 899162Notes

Reaction equation

HRID 899162 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 6-2 (253 mg, 0.66 mmol) and TPP (260 mg, 1.5 equivalents) in toluene was added tetrabromocarbon (242 mg, 1.1 equivalents) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography eluted with hexanes and EtOAc (2:1). The purified product [1-Bromomethyl-4-phthalimido-butyl]-carbamic acid benzyl ester (6-3) was obtained as a white solid, 263 mg (99%).

Workup

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

Sources & evidence

ORD record
ord-a057d0b8c0104425a3dc5b7710447875
Source dataset
uspto-grants-2008_04
Patent number
US07354923B2

Reaction notes

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