Carbon tetrabromide → Benzyl 5-Bromoamyl Ether

HRID 1837217Notes

Reaction equation

HRID 1837217 reaction equation
Br[C:2]([Br:5])(Br)Br.[CH2:6]([O:13][CH2:14][CH2:15][CH2:16][CH2:17]CO)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH2:6]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:2][Br:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2211945-(Benzyloxy)pentan-1-ol

Product 1

HCID 14221121Benzyl 5-Bromoamyl EtherYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

179 g of tetrabromomethane is added in portions to the solution of 85 g of 5-benzyloxy-pentan-1-ol and 143 g of triphenylphosphine in 720 ml of methylene chloride that is cooled to −15° C., and after the addition has been completed, it is stirred for 3 hours at 0° C. After the reaction mixture was concentrated by evaporation in a vacuum, the purification is carried out by chromatography on silica gel with a hexane-methylene chloride gradient. 71 g of 5-benzyloxy-1-bromo-pentane is obtained as an oil.

Workup

  1. additionafter the addition
  2. concentrationAfter the reaction mixture was concentrated by evaporation in a vacuum
  3. customthe purification

Sources & evidence

ORD record
ord-38eeecf991ed4ef28cc00c643d58743f
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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