(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride) → 8-Propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

HRID 1672102Notes

Reaction equation

HRID 1672102 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([C:11]3[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH3:24])[CH2:18][C:12]=3[C:13](=[O:17])[O:14]2)=[CH:9][CH:8]=1)(=O)=O.[F:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[C:32]([F:35])[C:33]=1[F:34].[OH-].[NH3+]N>O.C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:22]([CH:19]1[CH2:18][C:12]2[C:13](=[O:17])[O:14][C:15]3[C:10]([C:11]=2[CH2:21][CH2:20]1)=[CH:9][CH:8]=[C:7]([C:30]1[CH:29]=[C:28]([F:27])[C:33]([F:34])=[C:32]([F:35])[CH:31]=1)[CH:16]=3)[CH2:23][CH3:24]

Participants

7

Reactant 3

HCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)HCID 44558531Aminoammonium hydroxideHCID 579011976-oxo-8-propyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl trifluoromethanesulfonate

Product 1

HCID 166567888-Propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

10 g (25.6 mmol) of 6-oxo-8-propyl-7,8,9,10-tetrahydro-6H-benzo[c]-chromen-3-yl trifluoromethanesulfonate, 4.50 g (25.6 mmol) of 3,4,5-trifluorobenzeneboronic acid, 10.6 g (38.4 mmol) of sodium metaborate octahydrate, 360 mg (0.51 mmol) of bis(triphenylphosphine)palladium chloride and 50 μl of hydrazinium hydroxide are dissolved in 15 ml of water and 250 ml of THF, and the mixture is refluxed overnight. Water is added to the batch, which is extracted three times with dichloromethane. The combined org. phases are dried over sodium sulfate, the solvent is removed under reduced pressure, and the residue is filtered through silica gel and recrystallised, giving 8-propyl-3-(3,4,5-trifluorophenyl)-7,8,9,10-tetrahydrobenzo[c]chromen-6-one.

Workup

  1. extractionis extracted three times with dichloromethane
  2. dry with materialphases are dried over sodium sulfate
  3. customthe solvent is removed under reduced pressure
  4. filtrationthe residue is filtered through silica gel
  5. customrecrystallised

Sources & evidence

ORD record
ord-1fbd3b4cb2d047feade059ebf1386e11
Source dataset
uspto-grants-2011_08
Patent number
US07998541B2

Reaction notes

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