Isopropyl iodide → Methyl 2-(4-bromophenyl)-3-methylbutanoate

HRID 1525240Notes

Reaction equation

HRID 1525240 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH3:13][C:14]([O-])(C)[CH3:15].[K+].IC(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:14]([CH3:15])[CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 46855859Methyl 2-(4-bromophenyl)-3-methylbutanoateYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-(4-bromophenyl)acetate, 13-a, (2.29 g, 10 mmol) in DMF (40 ml) was added dropwise a mixture of t-BuOK (1.12 g, 10 mmol) in DMF (20 mL) with stirring at 0° C. under a nitrogen atmosphere. After stirring at 0° C. for 30 min, 2-iodopropane (1.70 g, 10 mmol) was added dropwise. Then the resulting solution was stirred overnight and ice-water was added. The aqueous layer was extracted by EA. The combined organic layers were washed by brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography to afford the title compound, 13-b, (1.3 g, 48%). 1H NMR (300 MHz, CDCl3) δ 0.70-0.72 (m, 3H), 1.02-1.04 (m, 3H), 2.27-2.32 (m, 1H), 3.10-3.14 (m, 1H), 3.65 (s, 3H), 7.19-7.24 (m, 2H), 7.42-7.45 (m, 2H). LC-MS: (M+H)+ 254, 256.

Workup

  1. stirringAfter stirring at 0° C. for 30 min
  2. stirringThen the resulting solution was stirred overnight
  3. extractionThe aqueous layer was extracted by EA
  4. washThe combined organic layers were washed by brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-0892e3544df246b6b32406941df6b35d
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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