Boron tribromide → HCID 59402772, compound

HRID 538501Notes

Reaction equation

HRID 538501 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][C:7]=1[C:14]([NH2:16])=[O:15]>C(Cl)Cl>[F:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[C:14]([NH2:16])=[O:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19028203HCID 19028203, compound

Product 1

HCID 59402772HCID 59402772, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide solution (1.0 M in CH2Cl2, 23.6 ml, 23.6 mmol, 2 equiv.) was added slowly, dropwise to stirred solution of 2-fluoro-5-methoxybenzenecarboxamide (2.0 g, 11.8 mmol, 1 equiv.) in CH2Cl2 (60 ml), at r.t., under N2. The reaction mixture was stirred at r.t. for 48 h. The solvent was removed under reduced pressure, the residue was dissolved in water (120 ml) and extracted with EtOAc (4×100 ml). The combined organic extracts were washed with water (2×100 ml), dried (Na2SO4) and filtered through a pad of silica gel. The filtrate was evaporated to dryness under reduced pressure, to give the desired compound as a grey solid (1.50 g, 82%).

Workup

  1. customat r.t.
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water (120 ml)
  4. extractionextracted with EtOAc (4×100 ml)
  5. washThe combined organic extracts were washed with water (2×100 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered through a pad of silica gel
  8. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4179eca97cb74f089849f08edda99562
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

Loading…