Ethyl isobutyrate → HCID 68379166, compound

HRID 2172719Notes

Reaction equation

HRID 2172719 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]([O:14][CH2:15][CH3:16])(=[O:13])[CH:10]([CH3:12])[CH3:11].[Br:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br>O1CCCC1.O>[Br:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][C:10]([CH3:12])([CH3:11])[C:9]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 7342Ethyl isobutyrateHCID 769652-Bromobenzyl bromideHCID 2724682Lithium diisopropylamide

Product 1

HCID 68379166HCID 68379166, compoundYield 169%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium diisopropylamide (2M in hexane, 1.5 mL, 3.0 mmol) was added to a solution of ethyl isobutyrate (233 mg, 2.01 mmol) in tetrahydrofuran (1 mL) at −78° C. and the reaction mixture was stirred at this temperature for 30 min. Then, a solution of 2-bromobenzyl bromide (250 mg, 1.00 mmol) in tetrahydrofuran (1 mL) was added dropwise. The reaction mixture was stirred at −78° C. for another 1 hr and then at room temperature overnight. The mixture was diluted with water and extracted with ethyl acetate. The combined organic fractions were washed with water, dried over sodium sulfate, and concentrated to give 482 mg of ethyl 3-(2-bromophenyl)-2,2-dimethylpropanoate as a yellow oil. The crude intermediate was used directly in the next step.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for another 1 hr
  2. customat room temperature
  3. customovernight
  4. extractionextracted with ethyl acetate
  5. washThe combined organic fractions were washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-677a24437fb248de99c9cbcdefc064e0
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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