Water → HCID 18002697, compound

HRID 1384885Notes

Reaction equation

HRID 1384885 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([F:15])[F:14])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:16]([F:19])([F:18])[F:17])=[N:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-:39].[Na+].O.[O:42]1[CH2:46]CCC1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:14][CH:13]([F:15])[O:12][C:9]1[C:8]2[N:7]=[C:6]([C:16]([F:19])([F:18])[F:17])[CH:5]=[CH:4][C:3]=2[C:2]([C:46]([OH:42])=[O:39])=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 18002685HCID 18002685, compound

Product 1

HCID 18002697HCID 18002697, compound

Reagents, catalysts & solvents 1

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-8difluoromethoxy-2-trifluoromethylquinoline (6.0 g), triphenylphosphine (0.3 g), bis(triphenylphosphine)palladium (II) chloride (0.15 g), 47% sodium hydroxide solution (4.5 g) and water (12 ml) in tetrahydrofuran (50 ml) was purged with carbon monoxide gas in a Parr pressure reactor at 7 bar. This was heated to 100° C. for 24 h. After cooling and venting the reaction mixture was partitioned between sodium hydroxide solution (1.5 g in 50 ml) and tert-butyl methyl ether (100 ml). The organic solution was extracted with sodium hydroxide solution (2×1.5 g in 50 ml). The combined aqueous extracts were stirred with activated charcoal (1.5 g) for 15 minutes and then filtered. The filtrate was acidified to pH 4 using 37% hydrochloric acid solution and the resultant cream precipitate isolated by filtration and washed with water (20 ml). The crude product was purified by recrystallisation from toluene to give the product (1.8 g) as a cream solid.

Workup

  1. customwas purged with carbon monoxide gas in a Parr pressure reactor at 7 bar
  2. temperatureAfter cooling
  3. customwas partitioned between sodium hydroxide solution (1.5 g in 50 ml) and tert-butyl methyl ether (100 ml)
  4. extractionThe organic solution was extracted with sodium hydroxide solution (2×1.5 g in 50 ml)
  5. filtrationfiltered
  6. customthe resultant cream precipitate isolated by filtration
  7. washwashed with water (20 ml)
  8. customThe crude product was purified by recrystallisation from toluene

Sources & evidence

ORD record
ord-14bed8845150456eadc338e8de7cc50e
Source dataset
uspto-grants-2001_07
Patent number
US06262070B1

Reaction notes

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