Carbon tetrabromide → HCID 19790700, compound

HRID 1668379Notes

Reaction equation

HRID 1668379 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:42]>C(#N)C.C(OCC)(=O)C>[CH2:14]([O:13][C:12](=[O:21])[NH:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][Br:42])=[CH:4][CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22337039HCID 22337039, compound

Product 1

HCID 19790700HCID 19790700, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl {2-[4-(hydroxymethyl)phenyl]ethyl}carbamate (1 g), triphenylphosphine (0.97 g) and carbon tetrabromide (1.2 g) in acetonitrile (1 ml) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-hexane (1:5, volume ratio)] and crystallized from hexane to give the title compound (0.96 g) as a colorless powder.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography [developing solvent:ethyl acetate-hexane (1:5, volume ratio)]
  5. customcrystallized from hexane

Sources & evidence

ORD record
ord-fbf0955f0a7348e6b7dda50dde6d24e1
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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