Carbon tetrabromide → HCID 89120206, compound

HRID 591265Notes

Reaction equation

HRID 591265 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]O)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40]>ClCCl>[Br:40][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69135266HCID 69135266, compound

Product 1

HCID 89120206HCID 89120206, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

{4-[3-(benzyloxy)propyl]benzyl alcohol (1.86 g, 7.31 mmol) was dissolved in 82 mL dichloromethane. The solution was cooled to 0° C. 3.25 g (12.41 mmol) triphenyl phosphine and 4.11 g (12.41 mmol) carbon tetrabromide were added to the solution. The ice bath was removed and the reaction was stirred for 1 h. The solution was concentrated in vacuo, to the residue was added tert-butyl methyl ether (100 mL) and the mixture was stirred at −20° C. for 30 min. The mixture was filtrated and the filtrate was concentrated in vacuo. The crude product was purified on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

  1. customThe ice bath was removed
  2. concentrationThe solution was concentrated in vacuo, to the residue
  3. additionwas added tert-butyl methyl ether (100 mL)
  4. stirringthe mixture was stirred at −20° C. for 30 min
  5. filtrationThe mixture was filtrated
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was purified on silica gel using a hexane/ethyl acetate gradient
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9c5c6f135d2a45a88b05815644a1e0c0
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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