Water → Ethyl 2-bromo-3-hydroxybutanoate

HRID 648271Notes

Reaction equation

HRID 648271 reaction equation
[C:1]([O:6]CC)(=O)/[CH:2]=C/C.O1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[OH2:15].[Br:16]N1C(=O)CCC1=O>CCOCC>[Br:16][CH:14]([CH:1]([OH:6])[CH3:2])[C:13]([O:12][CH2:11][CH3:10])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 67184N-bromobutanimideHCID 429065Ethyl trans-crotonate

Product 1

HCID 12541051Ethyl 2-bromo-3-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 10 g of ethyl crotonate, 40 ml of dioxane and 60 ml of water, at 0°, is slowly added 15 g of N-bromosuccinimide. After addition is complete, the reaction is allowed to stand at RT for 17 hr with stirring. The reaction is taken up in ether, washed with water and saturated sodium sulfite, dried over magnesium sulfate and evaporated under reduced pressure to yield ethyl 2-bromo-3-hydroxybutanoate.

Workup

  1. customat 0°
  2. additionAfter addition
  3. washwashed with water and saturated sodium sulfite
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4c31462e90ea477cb145a34ca79e7872
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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