Chloroform → HCID 86709464, compound

HRID 1501774Notes

Reaction equation

HRID 1501774 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-6fa7b8a83b7342798482a610fb357dfe
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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