Carbon tetrabromide → 2-[2-[2-Bromoethylthio]ethyl]-1,3-dioxolane

HRID 265307Notes

Reaction equation

HRID 265307 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][S:8][CH2:9][CH2:10]O.SC(O)C.[Br:16]CCC1OCCO1.[H-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br>C(#N)C>[Br:16][CH2:10][CH2:9][S:8][CH2:7][CH2:6][CH:2]1[O:3][CH2:4][CH2:5][O:1]1

Participants

8

Reactant 6

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 4713212Mercapto-ethanolHCID 190821812-[2-[1,3-Dioxolan-2-yl]ethylthio]ethanol

Product 1

HCID 190341872-[2-[2-Bromoethylthio]ethyl]-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred cooled (<0°) solution of 2-[2-[1,3-dioxolan-2-yl]ethylthio]ethanol (13.6 g, prepared by the condensation between mercaptoethanol and 2-[2-bromoethyl]-1,3-dioxolane employing sodium hydride) in dry acetonitrile (150 ml) was added triphenylphosphine (20 g) and carbon tetrabromide (38 g). The solution was stirred for 4 hours. The solvent was removed under reduced pressure and the residue pre-absorbed onto silica. The material was flash chromatographed over silica using 10% ethylacetate/petroleum ether as eluant to afford the subtitled compound as a clear oil (4.45 g). The material was used in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue pre-absorbed onto silica
  3. customchromatographed over silica using 10% ethylacetate/petroleum ether as eluant

Sources & evidence

ORD record
ord-8f54b5d2a7b94d1183f4229bc485bb5a
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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