Diethyl Ether → Methyl 3-(4-bromophenyl)butanoate

HRID 425433Notes

Reaction equation

HRID 425433 reaction equation
[CH3:1]COCC.[Li]C.[Br:8][C:9]1[CH:20]=[CH:19][C:12]([CH:13]=[CH:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1>C1COCC1.[Cu]I>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]([CH3:1])[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 8167732-Propenoic acid, 3-(4-bromophenyl)-, methyl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 66705619Methyl 3-(4-bromophenyl)butanoate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A flask under nitrogen atmosphere was charged with CuI (2.77 g, 14.54 mmol) and ether (50 mL). The slurry was cooled to 0 C in an ice-water bath before a solution of MeLi in THF (1.6M, 18.2 mL, 29.1 mmol) was added dropwise over 20 minutes. A clear solution formed. A solution of methyl 4-bromocinnamate (3.19 g, 13.2 mmol) in THF (30 mL) was added dropwise via syringe over 30 minutes, and the resulting reaction mixture was stirred at 0 C for 2 hours. Then the reaction was quenched with ammonium chloride and worked up. The resulting crude product was purified by MPLC (0 to 15% ethyl acetate in hexanes) to afford methyl 3-(4-bromophenyl)butanoate.

Workup

  1. additionwas added dropwise over 20 minutes
  2. customA clear solution formed
  3. customthe resulting reaction mixture
  4. customThen the reaction was quenched with ammonium chloride
  5. customThe resulting crude product was purified by MPLC (0 to 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-becb20755f144b9094406ed83064b2a2
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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