Phosphorus tribromide → 4-(Bromomethyl)-2-phenyl-1,3-dithiolane

HRID 1605064Notes

Reaction equation

HRID 1605064 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]1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 474291HCID 474291, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 370594-(Bromomethyl)-2-phenyl-1,3-dithiolaneYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

  1. dry with materialAfter drying over MgSO4 the solvent
  2. customwas removed under vacuum
  3. 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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