Carbon tetrabromide → HCID 22981310, compound

HRID 1861961Notes

Reaction equation

HRID 1861961 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][C:9]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][Br:38])=[CH:10][C:9]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22981315tert-butyl N-[4-(hydroxymethyl)-2-methylphenyl]carbamate

Product 1

HCID 22981310HCID 22981310, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (1.035 g) obtained in Example 518 was dissolved in methylene chloride (20 ml) and to the solution, triphenylphosphine (1.38 g) and carbon tetrabromide (1.74 g) were successively added under ice cooling. The reaction mixture was stirred for 30 min under ice cooling, then stirred at room temperature for 30 min and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=5:1) to give 476.6 mg of the titled compound (yield, 36%).

Workup

  1. additionwere successively added under ice cooling
  2. stirringstirred at room temperature for 30 min
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-4a27f0bff4a0406d827c1f1f587b975d
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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