Oxalyl chloride → HCID 66610889, compound

HRID 625753

Reaction equation

HRID 625753 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=O.C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:21]=1[C:22]([NH2:24])=[O:23]>C(Cl)Cl.CN(C=O)C.N1C=CC=CC=1>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([NH:19][C:20]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:21]=1[C:22]([NH2:24])=[O:23])=[O:5]

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 102410042-Amino-4-fluorobenzamideHCID 16217752Bromo(4-fluorophenyl)acetic acid

Product 1

HCID 66610889HCID 66610889, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromo-2-(4-fluorophenyl)acetic acid (425 mg, 1.82 mmol) in DCM (5 mL) and DMF (0.05 mL) was added oxalyl chloride (0.17 mL, 1.91 mmol) and the solution was stirred for 0.75 h. The solution was then cooled to 0° C. and a solution of 2-amino-4-fluorobenzamide (267 mg, 1.73 mmol) in pyridine (1 mL) was added. The solution was stirred at rt for 1 h and then evaporated. The crude residue was partitioned between EtOAc and 2 N HCl. The EtOAc layer was evaporated to give 2-(2-bromo-2-(4-fluorophenyl)acetamido)-4-fluorobenzamide as a crude oil which was used without further purification. (420 mg, 62%). LC-MS (ESI) m/z 369 (M−H)—.

Workup

  1. stirringThe solution was stirred at rt for 1 h
  2. customevaporated
  3. customThe crude residue was partitioned between EtOAc and 2 N HCl
  4. customThe EtOAc layer was evaporated

Sources & evidence

ORD record
ord-6d6a742a0aa540a0a63b152078c2fb70
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Linked notes

Loading…