Carbon tetrabromide → HCID 86750380, compound

HRID 862844Notes

Reaction equation

HRID 862844 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-01dde40333d74cbaa910c1565a2bd53f
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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