Phosphorus tribromide → 1,3-Dithiolane, 4-bromomethyl-2-phenyl-
Reaction equation
O[CH2:2][CH:3]1[CH2:7][S:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4]1.P(Br)(Br)[Br:15].C([O-])(O)=O.[Na+]>CCOCC>[Br:15][CH2:2][CH:3]1[CH2:7][S:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-Hydroxymethyl 2-phenyl 1,3-dithiolane (30 g., 0.14 mole) was suspended in 150 ml of ether and cooled to 0°C. Phosphorus tribromide (15 g., 0.053 mole) were added over a 1.5 hour period and the mixture was stirred at ambient temperature with 5% aqueous NaHCO3 until neutral (ph = 7). After drying over MgSO4 the solvent was removed under vacuum to yield 38 g. (99%) of desired product.
Workup
- dry with materialAfter drying over MgSO4 the solvent
- customwas removed under vacuum
- customto yield 38 g
Sources & evidence
- ORD record
- ord-9993c761b10e4d94a5509ca8e7140f1c
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03948944
Reaction notes
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