(+-)-2-Butanol → 2-Methylpropyl 2-bromoacetate

HRID 1089195Notes

Reaction equation

HRID 1089195 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH2:6](N(CC)CC)C.[CH:13]([OH:17])([CH2:15][CH3:16])C>O1CCCC1>[Br:1][CH2:2][C:3]([O:17][CH2:13][CH:15]([CH3:16])[CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 6568(+-)-2-ButanolHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 5219062-Methylpropyl 2-bromoacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

41 g (0.2 mol) of bromoacetyl bromide are dissolved in 400 ml of tetrahydrofuran, and a mixture of 36 ml of triethylamine and 15 g of sec-butanol, dissolved in 20 ml of tetrahydrofuran, is added at 20° C. The mixture is stirred at 20° C. for 8 hours and extracted using water/methylene chloride. After drying, rotary evaporation and distillation, 13.9 g (36% of theory) of 2-methyl-propyl bromoacetate are obtained.

Workup

  1. additionis added at 20° C
  2. extractionextracted
  3. customAfter drying
  4. customrotary evaporation and distillation, 13.9 g (36% of theory) of 2-methyl-propyl bromoacetate
  5. customare obtained

Sources & evidence

ORD record
ord-0bba437364774c9da347c1ba10b5612b
Source dataset
uspto-grants-1990_10
Patent number
US04965286

Reaction notes

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