Iodoethane → Ethyl 2-(4-bromophenyl)butanoate

HRID 735692Notes

Reaction equation

HRID 735692 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[Li+].[CH3:15][CH:16]([N-]C(C)C)C.C(I)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:15][CH3:16])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2724682Lithium diisopropylamideHCID 7020609Ethyl 2-(4-bromophenyl)acetate

Product 1

HCID 57082745Ethyl 2-(4-bromophenyl)butanoateYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-bromophenyl)acetate (972 mg, 4 mmol) in 10 mL dry THF at −78° C. was added LDA (2 M, 2 mL, 4 mmol). The solution was warmed to rt and stirred 2 h, then was recooled to −78° C. EtI (0.52 mL) was added, then the reaction was stirred rt for 16 h. The reaction was quenched with sat. NH4Cl, then extracted with EtOAc (3×20 mL). The organic layer washed with brine, then dried (Na2SO4). Purification via flash chromatography (0-20% EtOAc in hexanes) gives 75A (228 mg, 21%). MS (ESI) m/z 271.0 (M+H)+.

Workup

  1. customwas recooled to −78° C
  2. stirringthe reaction was stirred rt for 16 h
  3. customThe reaction was quenched with sat. NH4Cl
  4. extractionextracted with EtOAc (3×20 mL)
  5. washThe organic layer washed with brine
  6. dry with materialdried (Na2SO4)
  7. customPurification via flash chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-baef265f2af64fa49172de9f3492f428
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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