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

HRID 908526Notes

Reaction equation

HRID 908526 reaction equation
[CH3:1][C:2]1([CH3:11])[O:7][CH2:6][CH:5]([CH2:8][CH2:9]O)[CH2:4][O:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:32][CH2:9][CH2:8][CH:5]1[CH2:6][O:7][C:2]([CH3:11])([CH3:1])[O:3][CH2:4]1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 118160112-(2,2-Dimethyl-1,3-dioxan-5-yl)ethanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 32 (84 g, 0.528 mol) in dry DMF (500 mL) was added triphenylphosphine (207 g, 0.79 mol) with vigorous stirring until it becomes a clear solution. The mixture was cooled to 0° C. and added CBr4 (260 g, 0.79 mol) portion wise over a period of 30 min and allowed to stir at RT for 5 h. The reaction mixture was cooled to 0° C., added saturated NaHCO3 solution (200 mL) and extracted with hexane (4×200 mL). The combined organic layer was dried, concentrated under vacuum and the crude title compound (117 g) was used for next reaction without any purification. TLC: Pet. ether/EtOAc, 7:3, Rf=0.6

Workup

  1. stirringto stir at RT for 5 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionextracted with hexane (4×200 mL)
  4. customThe combined organic layer was dried
  5. concentrationconcentrated under vacuum
  6. customthe crude title compound (117 g) was used for next reaction without any purification

Sources & evidence

ORD record
ord-8a9400e2ee204391b432642c46834d37
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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