Ammonia → BenzenepropanaMide, 2-broMo-

HRID 2194874Notes

Reaction equation

HRID 2194874 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=O.C(Cl)(=O)C(Cl)=O.[NH3:19].C1OCCOC1>C(Cl)Cl.C1(C)C=CC=CC=1.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([NH2:19])=[O:12]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 65578Oxalyl chlorideHCID 3160103-(2-Bromophenyl)propionic acid

Product 1

HCID 12226096BenzenepropanaMide, 2-broMo-

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of commercially available 3-(2-bromophenyl)propanoic acid (1 eq.) in CH2Cl2 (0.22M) at room temperature was added oxalyl chloride (16 eq) and a catalytic amount of DMF. The mixture was stiffed for 2 h, diluted with toluene (0.022M) and concentrated. To the residue diluted in CH2Cl2 (0.1M) at 0° C. was added ammonia (0.5M in dioxanne (3 eq.). The mixture was stiffed 2 h at room temperature, concentrated, quenched with aqueous NaOH 1N and then extracted with EtOAc. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Recrystallization in Et2O/hexane (1:1) afforded the desired compound as a white solid.

Workup

  1. concentrationconcentrated
  2. additionTo the residue diluted in CH2Cl2 (0.1M) at 0° C.
  3. waitThe mixture was stiffed 2 h at room temperature
  4. concentrationconcentrated
  5. customquenched with aqueous NaOH 1N
  6. extractionextracted with EtOAc
  7. extractionThe organic extract
  8. washwas washed with water, brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customRecrystallization in Et2O/hexane (1:1)

Sources & evidence

ORD record
ord-7a1e5b57cfbb4ef88346960308e11437
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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