Triethylamine → Benzenepropanoic acid, 3-bromo-3-oxo-, ethyl ester

HRID 896065Notes

Reaction equation

HRID 896065 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([O-:5])=O.[K+].C(N(CC)CC)C.[Cl-].[Mg+2].[Cl-].[Br:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)C(Cl)=O>C(#N)C>[CH2:8]([O:7][C:1](=[O:6])[CH2:2][C:3]([C:29]1[CH:28]=[CH:24][CH:23]=[C:22]([Br:21])[CH:30]=1)=[O:5])[CH3:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 74377Benzoyl chloride, 3-bromo-HCID 3446434Potassium ethyl malonateHCID 5360315Magnesium Chloride

Product 1

HCID 179368Benzenepropanoic acid, 3-bromo-3-oxo-, ethyl esterYield 99.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To potassium ethyl malonate (3.25 g, 19.13 mmol) in acetonitrile (50 mL) was sequentially added triethyl amine (4.1 mL, 29.16 mmol) and magnesium chloride (2.16 g, 22.78 mmol) at room temperature. After stirring the reaction mixture at room temperature for 2 hours, 3-bromobenzoyl chloride (2.0 g, 9.11 mmol) was added and the mixture was heated at 60° C. for 18 hours, concentrated under reduced pressure and partitioned between ethyl acetate (100 mL) and 1N HCl (25 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to yield the title compound (2.45 g, 99 %). 1H NMR (CDCl3): δ 8.1 (s, 1H), 7.85 (d, 1H), 7.7 (d, 1H), 7.35 (t, 1H), 4.3 (m, 2H), 3.4 (s, 1H), 1.3 (m, 3H).

Workup

  1. customat room temperature
  2. temperaturethe mixture was heated at 60° C. for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. custompartitioned between ethyl acetate (100 mL) and 1N HCl (25 mL)
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-638cada0218649ea87d88bdef96a0f7a
Source dataset
uspto-grants-2005_07
Patent number
US06919335B2

Reaction notes

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