2,6-Dichloro-N-[[2-fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-aniline → 2,4-Dichloro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol

HRID 1771682Notes

Reaction equation

HRID 1771682 reaction equation
[Cl:1][C:2]1[C:23]([O:24]C)=[CH:22][CH:21]=[C:20]([Cl:26])[C:3]=1[NH:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:9]=[CH:8][C:7]=1[F:19]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([NH:4][CH2:5][C:6]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[CH:9]=[CH:8][C:7]=2[F:19])=[C:20]([Cl:26])[CH:21]=[CH:22][C:23]=1[OH:24]

Participants

3

Reactant 1

HCID 894437042,6-Dichloro-N-[[2-fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-aniline

Product 1

HCID 894452242,4-Dichloro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenolYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,6-dichloro-N-[[2-fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-aniline (200 mg, 0.5 mmol, 1.0 eq) in DCM (15 mL) at 0° C. was added borontribromide (640 mg, 2.5 mmol, 5.0 eq) portion-wise. The reaction was stirred at room temperature overnight then poured into ice. The mixture was extracted with EtOAc and the combined organic extracts were dried, (Na2SO4) filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (Petroleum ether:EtOAc, 20:1) to give the title compound (150 mg, 77%).

Workup

  1. additionthen poured into ice
  2. extractionThe mixture was extracted with EtOAc
  3. customthe combined organic extracts were dried
  4. filtration(Na2SO4) filtered
  5. customevaporated in vacuo
  6. customThe residue obtained
  7. customwas purified by column chromatography (Petroleum ether:EtOAc, 20:1)

Sources & evidence

ORD record
ord-91593eb10c49414fb25a2c9f7b52856f
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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