Carbon tetrabromide → HCID 86750380, compound

HRID 617867Notes

Reaction equation

HRID 617867 reaction equation
[CH2:1]([S:13][CH2:14][CH2:15][CH2:16]O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:19][CH2:16][CH2:15][CH2:14][S:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 41722041-Propanol, 3-(dodecylthio)-

Product 1

HCID 86750380HCID 86750380, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Dodecylthiopropanol (3.0 g) was dissolved in 60 ml of dichloromethane and 7.66 g of carbon tetrabromide and 5.44 g of triphenylphosphine were added thereto under ice-cooling. The mixture was stirred under ice-cooling for 15 minutes. The reaction mixture was concentrated, and the residue was extracted with hexane. The extract was concentrated and purified by silica gel column chromatography using hexane as an eluent to give 3.255 g of pale yellow, oily 3-bromopropyldodecyl sulfide.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling for 15 minutes
  3. concentrationThe reaction mixture was concentrated
  4. extractionthe residue was extracted with hexane
  5. concentrationThe extract was concentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-06bd222e3a7f40c398c9ebb2350754f2
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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