Chloroform → HCID 86709464, compound

HRID 1848455Notes

Reaction equation

HRID 1848455 reaction equation
[C:1]([CH:4]([CH:10]([CH3:12])[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2].[Br:13]Br.C(Cl)(Cl)Cl.C(OCC)(=O)C>O>[Br:13][CH2:2][C:1](=[O:3])[CH:4]([CH:10]([CH3:11])[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 24408BromineHCID 95544Butanoic acid, 2-acetyl-3-methyl-, ethyl ester

Product 1

HCID 86709464HCID 86709464, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-acetyl-3-methylbutanoate (5.10 g, 29.6 mmol) in water (10 mL) at 0° C. was added bromine (1.53 mL, 29.6 mmol) dropwise over 2 h. Chloroform (30 mL) was added and the resulting solution was stirred at rt for 16 h. Ethyl acetate (300 mL) was added to the reaction solution and the organic phase was dried over sodium sulfate and concentrated to give the title compound. 1HNMR (500 MHz, CDCl3), δ4.300-4.282 (m, 2H), 2.601-2.575 (m, 1H), 2.406 (s, 2H), 1.331-1.303 (t, J=7.1 Hz, 3H), 1.085-1.072 (d, J=6.5 Hz, 3H), 1.048-1.035 (d, J=6.7 Hz, 3H).

Workup

  1. dry with materialthe organic phase was dried over sodium sulfate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-be6ab9a59ad2407abbeea261dbed9c1d
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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