Benzyl Bromide → Benzyl 4-(4-bromophenyl)-4-oxobutanoate

HRID 80391Notes

Reaction equation

HRID 80391 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:22])[CH2:17][CH2:18][C:19]([O:21][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:20])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 806463-(4-Bromobenzoyl)propionic acid

Product 1

HCID 57610959Benzyl 4-(4-bromophenyl)-4-oxobutanoateYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (9.98 g, 58.3 mmol) was added to a solution of 4-(4-bromophenyl)-4-oxobutanoic acid (15.0 g, 58.3 mmol) and K2CO3 (3.5 g, 58.3 mmol) in DMF (300 mL) and stirred for 18 hours. The reaction mixture was partitioned between water (200 mL) and ethyl acetate (500 mL). Sat'd NaHCO3 soln (20 mL) was added and the aqueous layer extracted with ethyl acetate (2×) and the combined organic layers were washed with brine and dried and filtered. Concentration gave Example J5, benzyl 4-(4-bromophenyl)-4-oxobutanoate 16 g (79%) which was used without further purification. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=8.6 Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.35-7.34 (m, 5H), 5.14 (s, 2H), 3.27 (t, J=6.7 Hz, 2H), 2.81 (t, J=6.7 Hz, 2H). HRMS: Anal. C17H16BrNO3 Calcd. 347.0277; found: 347.0283 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between water (200 mL) and ethyl acetate (500 mL)
  2. additionSat'd NaHCO3 soln (20 mL) was added
  3. extractionthe aqueous layer extracted with ethyl acetate (2×)
  4. washthe combined organic layers were washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationConcentration

Sources & evidence

ORD record
ord-84a5152c782b44fdb0429b093a9b0395
Source dataset
uspto-grants-2014_09
Patent number
US08846023B2

Reaction notes

Loading…