Water → 1,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-
Reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[O:6][CH2:5]1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>CN(C)C=O.C(=O)(O)[O-].[Na+]>[Br:13][CH2:2][CH2:3][CH:4]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[O:6][CH2:5]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To an ice-cooled solution of 5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan (6.08 g, 38 mmol) and carbon tetrabromide (18.90 g, 57 mmol) in N,N-dimethylformamide (110 ml); triphenylphosphine (14.95 g, 57 mmol) was added. The solution was stirred for 0.5 hour at 0° C. The solution was then diluted with saturated aqueous sodium bicarbonate (55 ml) followed by water (55 ml), and was extracted with hexane (2×150 ml). The combined organic layers were dried (magnesium sulphate) and the solvent removed. The residue was placed under high vacuum for 2 hours to remove bromoform. The residue was taken up in a small amount of hexane, filtered and the solvent removed to afford 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxan (7.40 g, 87%) as a colourless oil which crystallised on cooling, m.p. ca. 18° C.
Workup
- extractionwas extracted with hexane (2×150 ml)
- dry with materialThe combined organic layers were dried (magnesium sulphate)
- customthe solvent removed
- waitThe residue was placed under high vacuum for 2 hours
- customto remove bromoform
- filtrationfiltered
- customthe solvent removed
Sources & evidence
- ORD record
- ord-42e894eed23a4899ad9c49bc45244796
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06579981B1
Reaction notes
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