Dichloromethane → Triphenylphosphine Oxide

HRID 1507595Notes

Reaction equation

HRID 1507595 reaction equation
[CH:1]1([S:4][CH2:5][CH2:6][CH2:7][OH:8])[CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:10].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.ClCCl>CCCCC>[Br:10][CH2:7][CH2:6][CH2:5][S:4][CH:1]1[CH2:3][CH2:2]1.[CH:30]1[CH:31]=[CH:32][C:27]([P:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:8])=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 90046341HCID 90046341, compound

Product 2

HCID 13097Triphenylphosphine OxideYield 188.4%HCID 90046305HCID 90046305, compound

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a suspension of 3-(cyclopropylthio)propan-1-ol (1.68 g, 12.7 mmol) and CBr4 (5.06 g, 15.2 mmol) in pentane (13 ml) was added triphenylphosphine (4.00 g, 15.2 mmol) portionwise under icecooling. Dichloromethane (7 ml) was added and the suspension was stirred for 4 hours. The reaction mixture was filtered and washed with pentane. The obtained solution was concentrated in vacuo. The title compound was obtained as a mixture with TPPO as brown semisolid (6.66 g). The material was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with pentane
  3. concentrationThe obtained solution was concentrated in vacuo

Sources & evidence

ORD record
ord-db8f180bf8ab407c824c81980b81e9a7
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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