Potassium Carbonate → 8-Bromooctyl benzoylbutyrate

HRID 1510608Notes

Reaction equation

HRID 1510608 reaction equation
[C:1]([CH:9]([CH2:13][CH3:14])[C:10]([OH:12])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:1]([CH:9]([CH2:13][CH3:14])[C:10]([O:12][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][Br:15])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 783101,8-DibromooctaneHCID 21651867alpha-Ethyl-beta-oxobenzenepropanoic acid

Product 1

HCID 675331908-Bromooctyl benzoylbutyrate

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of benzoylbutyric acid (9.0 g, 46.8 mmol), 1,8-dibromooctane (31.5 g, 117.0 mmol), potassium carbonate (16.4 g, 117.0 mmol), dry DMF (70 mL), and a catalytic amount of tetra-n-butylammonium iodide (1.0 mol %) was stirred and heated at 50° C. overnight. The solvent was evaporated. The residue was washed with dilute HCl and then extracted into ether, washed with brine, and dried with MgSO4. The solvent and excess 1,8-dibromooctane were removed under reduced pressure. The crude product was chromatographed on silica using 0-20% ethyl acetate in hexane. Isolated yield=13.5 g (75%) as a colorless liquid. 1H NMR (CDCl3, 200 MHz): δ ppm 7.95 (dd, J=8.24, 1.49 Hz, 2H), 7.47 (m, 3H), 4.05 (t, J=6.64 Hz, 2H), 3.37 (t, J=6.81, 2H), 3.04 (t, J=7.13 Hz, 2H), 2.42 (t, J=7.20 Hz, 2H), 2.01 (m, 2H), 1.82-1.73 (m, 2H), 1.69-1.51 (m, 2H), 1.47-1.21 (m, 8H). 13C NMR (CDCl3, 50.28 MHz): δ 199.29, 173.25, 136.75, 133.00, 128.52, 127.94, 64.41, 37.40, 33.90, 33.34, 32.67, 28.96, 28.50, 27.97, 25.76, 19.34. HRMS (EI) m/z: 405 ((M+Na)+•). Elemental analysis: Calculated for C19H27BrO3: C, 59.53; H, 7.10; Br, 20.85; O, 12.52. Found: C, 59.77; H, 7.52.

Workup

  1. customThe solvent was evaporated
  2. washThe residue was washed with dilute HCl
  3. extractionextracted into ether
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. customThe solvent and excess 1,8-dibromooctane were removed under reduced pressure
  7. customThe crude product was chromatographed on silica using 0-20% ethyl acetate in hexane
  8. customIsolated yield=13.5 g (75%) as a colorless liquid

Sources & evidence

ORD record
ord-3cab7e93d4e14fbba64c41f69d3f4aa3
Source dataset
uspto-grants-2012_07
Patent number
US08211996B2

Reaction notes

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