Water → 1,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-

HRID 1368673Notes

Reaction equation

HRID 1368673 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]1

Participants

7

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 118160112-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanol

Product 1

HCID 1789881,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-Yield 87.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

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), triphenyl-phosphine (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

  1. additionwas added
  2. extractionwas extracted with hexane (2×150 ml)
  3. dry with materialThe combined organic layers were dried (magnesium sulphate)
  4. customthe solvent removed
  5. waitThe residue was placed under high vacuum for 2 hours
  6. customto remove bromoform
  7. filtrationfiltered
  8. customthe solvent removed

Sources & evidence

ORD record
ord-6cb936272990449294e5b719194c552c
Source dataset
uspto-grants-2003_06
Patent number
US06573378B1

Reaction notes

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