Carbon tetrabromide → HCID 53884556, compound

HRID 343817Notes

Reaction equation

HRID 343817 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([C:21]([O:23][CH3:24])=[O:22])[CH2:12][CH2:13]OC1CCCCO1.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:26][CH2:13][CH2:12][CH:11]([C:21]([O:23][CH3:24])=[O:22])[C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53640125HCID 53640125, compound

Product 1

HCID 53884556HCID 53884556, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product of step (a) (2.0 g, 6.1 mmol) and carbon tetrabromide (2.83 g, 8.5 mmol) were dissolved in dichloromethane (30 ml) and cooled to 0° C. under nitrogen. Triphenylphosphine (4.48 g, 17.1 mmol) was added portionwise turning the reaction mixture deep yellow. After stirring at room temperature for 18 hours the reaction mixture was concentrated under reduced pressure. The oil was purified by flash chromatography on silica gel eluting with 1:1 dichloromethane:hexane to give 1-bromo-3-(methoxycarbonyl)-3-(2-naphthyl)propane as a white solid (0.56 g, 30%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe oil was purified by flash chromatography on silica gel eluting with 1:1 dichloromethane

Sources & evidence

ORD record
ord-0d5b63e6dee74a6db61c795edd31f864
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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