Boron tribromide → HCID 18432940, compound

HRID 2305549Notes

Reaction equation

HRID 2305549 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 7370144-chloro-6-methoxy-2-phenylquinoline

Product 1

HCID 18432940HCID 18432940, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −78° C. solution of 4-chloro-6-methoxy-2-phenyl-quinoline (1.0 g, 3.7 mmol) in CH2Cl2 (25 ml) was added dropwise BBr3 (11.1 ml, 11.1 mmol, 1M in CH2Cl2). Reaction mixture was then allowed to warm to room temperature. After 4.5 hours, mixture was cooled to −10° C. and quenched slowly with a saturated solution of NaHCO3 (70 ml). The aqueous phase was extracted with ethyl acetate (3×100 ml). Combined organic phases were dried over Na2SO4 and concentrated. The solid residue was refluxed during 1 hour in ethyl acetate (30 ml), cooled to room temperature, and filtered. Filtrate was concentrated and chromatographed over silica gel (hexane-ethyl acetate, 4:1) to provide 4-chloro-2-phenyl-quinolin-6-ol (0.375 g, 40%) as a yellow solid, m. p. 180-181° C., MS: m/e=255 (M+).

Workup

  1. customReaction mixture
  2. temperaturemixture was cooled to −10° C.
  3. customquenched slowly with a saturated solution of NaHCO3 (70 ml)
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×100 ml)
  5. dry with materialCombined organic phases were dried over Na2SO4
  6. concentrationconcentrated
  7. temperatureThe solid residue was refluxed during 1 hour in ethyl acetate (30 ml)
  8. temperaturecooled to room temperature
  9. filtrationfiltered
  10. concentrationFiltrate was concentrated
  11. customchromatographed over silica gel (hexane-ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-fd794eb9da644959826e0f0eb7180b8b
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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