Water → HCID 89445280, compound

HRID 1771808Notes

Reaction equation

HRID 1771808 reaction equation
[F:1][C:2]1[C:3]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:27])=[C:4]([C:7]([O:10]C)=[CH:8][CH:9]=1)[C:5]#[N:6].B(Br)(Br)Br.O>C(Cl)Cl>[F:1][C:2]1[C:3]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)[CH:17]=[CH:16][C:15]=2[F:27])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 89443811HCID 89443811, compound

Product 1

HCID 89445280HCID 89445280, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-2-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-6-methoxy-benzonitrile (560 mg, 1.5 mmol, 1 eq) in CH2Cl2 (30 mL) was added BBr3 (1.14 g, 4.5 mmol, 3 eq) and the reaction was stirred overnight. The mixture was then poured into water, and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 10:1 to 5:1) to give the title compound as a yellow oil (360 mg, 68%).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue obtained
  7. customwas purified by column chromatography (petroleum ether:EtOAc, 10:1 to 5:1)

Sources & evidence

ORD record
ord-4a19a7145b134c4c9c88544a02ac3645
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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