Boron tribromide → Perfluorophenyl 1-(4-bromo-5-fluoro-2-hydroxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

HRID 1504373Notes

Reaction equation

HRID 1504373 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([O:22][C:23]4[C:28]([F:29])=[C:27]([F:30])[C:26]([F:31])=[C:25]([F:32])[C:24]=4[F:33])(=[O:21])=[O:20])=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:34])=[C:4]([O:35]C)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([O:22][C:23]4[C:24]([F:33])=[C:25]([F:32])[C:26]([F:31])=[C:27]([F:30])[C:28]=4[F:29])(=[O:20])=[O:21])=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:34])=[C:4]([OH:35])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 117736986Perfluorophenyl 1-(4-bromo-5-fluoro-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

Product 1

HCID 117737059Perfluorophenyl 1-(4-bromo-5-fluoro-2-hydroxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of perfluorophenyl 1-(4-bromo-5-fluoro-2-methoxyphenyl)-2-oxo-1,2-dihydroquinoline-6-sulfonate (5.0 g, 8.41 mmol) in DCM (56.1 ml) was added boron tribromide (0.811 ml, 8.41 mmol) at room temperature. The resulting mixture was stirred for 48 hr. The crude mixture was transferred to a sep. funnel containing saturated aqueous bicarb and the aqueous layer was washed 3× with DCM. The organic layers were combined, dried with MgSO4, filtered and concentrated to a white solid. The product was concentrated to a solid, redissolved in toluene (100 mls) and heated to 100° C. for 1 hour to racemize the product. The solution was then cooled to room temperature and concentrated to a solid (4.4 g, 89% crude yield). m/z (ESI) 582.0 (M+1)+.

Workup

  1. additionfunnel containing saturated aqueous bicarb
  2. washthe aqueous layer was washed 3× with DCM
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid
  6. concentrationThe product was concentrated to a solid
  7. dissolutionredissolved in toluene (100 mls)
  8. temperatureThe solution was then cooled to room temperature
  9. concentrationconcentrated to a solid (4.4 g, 89% crude yield)

Sources & evidence

ORD record
ord-38485bd0dcc6455ea0dc07aab54c6d62
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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