Dichloromethane → Ethyl 3-bromo-2-(hydroxyimino)propanoate

HRID 2307800Notes

Reaction equation

HRID 2307800 reaction equation
[Br:1][CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[NH2:11][OH:12].C(Cl)Cl>O.C(Cl)(Cl)Cl>[CH2:7]([O:6][C:4](=[O:5])[C:3](=[N:11][OH:12])[CH2:2][Br:1])[CH3:8]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 66144Ethyl bromopyruvateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 53428735Ethyl 3-bromo-2-(hydroxyimino)propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

Ethyl bromopyruvate (5.0 mL, 39.8 mmol) was added to hydroxylamine hydrochloride (2.52 g, 36.2 mmol) in H2O (10 mL) and CHCl3 (10 mL). The reaction mixture was capped and stirred overnight at 23° C. at which time CH2Cl2 and H2O were added, the layers separated, the organics dried over Na2SO4, and the volatiles removed on a rotary evaporator to yield 7.58 g (100%) of as a white solid. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.26 (t, J=7.12 Hz, 3 H) 4.20 (s, 2 H) 4.24 (m, 2 H) 13.19 (s, 1 H).

Workup

  1. customThe reaction mixture was capped
  2. additionwere added
  3. customthe layers separated
  4. dry with materialthe organics dried over Na2SO4
  5. customthe volatiles removed on a rotary evaporator
  6. customto yield 7.58 g (100%) of as a white solid

Sources & evidence

ORD record
ord-11f7e7cf57074f36a424d88f723a6e1d
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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