Pyridine → 2,2-Dibromopropyl carbonochloridate
Reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[Br:5][C:6]([Br:10])([CH3:9])[CH2:7][OH:8].N1C=CC=CC=1>C(Cl)Cl>[Br:5][C:6]([Br:10])([CH3:9])[CH2:7][O:8][C:1]([Cl:4])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
16 ml (0.22 mol) of liquid phosgene are condensed into 33 g (0.15 mol) of 2,2-dibromopropanol in 150 ml of CH2Cl2, at -20° C, and 12 ml (0.15 mol) of pyridine in 15 ml of CH2Cl2 are then added slowly dropwise at -20° C to -5° C and the mixture is stirred for a further 2 hours at 20° C. The solution is washed, at 0° C, with water, 5% strength sulphuric acid and H2O and dried (Na2SO4) and the solvent is stripped off (46.1 g of crude product). Vacuum distillation gives 36.3 g (86%) of 2,2-dibromopropoxycarbonyl chloride as a colorless liquid. Boiling point12 = 81°-86° C.
Workup
- washThe solution is washed, at 0° C, with water, 5% strength sulphuric acid and H2O
- dry with materialdried (Na2SO4)
- distillationVacuum distillation
Sources & evidence
- ORD record
- ord-91608cc15eb1460282ecbe32fca775a7
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04111933
Reaction notes
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