Hydrochloric Acid → 2-Propyl-6-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydronaphthalene

HRID 352279Notes

Reaction equation

HRID 352279 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]2)(=O)=O.[F:22][C:23]1[CH:24]=[C:25](OB(O)O)[CH:26]=[C:27]([F:30])[C:28]=1[F:29].FC1C=C(Br)C=C(F)C=1F.[Mg].COB(OC)OC.Cl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:17]([CH:12]1[CH2:11][CH2:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:25]3[CH:24]=[C:23]([F:22])[C:28]([F:29])=[C:27]([F:30])[CH:26]=3)[CH:8]=2)[CH2:13]1)[CH2:18][CH3:19]

Participants

11

Reactant 7

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 62657Potassium Phosphate, TribasicHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 5462224MagnesiumHCID 21870694HCID 21870694, compoundHCID 227090452-Propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate

Product 1

HCID 227090512-Propyl-6-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydronaphthaleneYield 13.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.8 g of the produced 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate, 3.0 g of 3,4,5-trifluorophenylboric acid (this compound was produced by reacting a Grignard reagent prepared from 3,4,5-trifluorobromobenzene and magnesium, with trimethoxy borane, and then performing a hydrolysis with dilute hydrochloric acid), 0.13 g of tetrakis(triphenylphosphine)palladium(0), and 3.6 g of potassium phosphate in 20 ml of dimethyl formamide (DMF) was stirred for 10 hours at 80° C. The mixture was subsequently cooled to room temperature, 20 ml of water was added, the mixture was extracted with toluene, and the organic layer was washed subsequently with water and then a saturated aqueous solution of sodium chloride, and subsequently dried over anhydrous sodium sulfate. The crude product obtained by removal of the solvent by evaporation was purified by silica gel column chromatography (hexane) and then recrystallized 3 times from ethanol to obtain 0.5 g of 2-propyl-6-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydronaphthalene.

Workup

  1. customwas produced
  2. temperatureThe mixture was subsequently cooled to room temperature
  3. extractionthe mixture was extracted with toluene
  4. washthe organic layer was washed subsequently with water
  5. dry with materiala saturated aqueous solution of sodium chloride, and subsequently dried over anhydrous sodium sulfate
  6. customThe crude product obtained by removal of the solvent by evaporation
  7. customwas purified by silica gel column chromatography (hexane)
  8. customrecrystallized 3 times from ethanol

Sources & evidence

ORD record
ord-f165dfb7de764579bc3f25abc5a6e8be
Source dataset
uspto-grants-2004_06
Patent number
US06746728B1

Reaction notes

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