Sodium Carbonate → HCID 117665489, compound

HRID 1482445Notes

Reaction equation

HRID 1482445 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].C(=O)([O-])[O-].[Na+].[Na+].[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[C:25]([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH2:4][CH2:5][CH2:6][C:7]3=[O:12])[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 108895725-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 117665489HCID 117665489, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

A 50 mL Schlenk tube was charged with 5-bromo-3,4-dihydronaphthalen-1(2H)-one (5-bromo-1-tetralone [Aldrich], 488 mg, 2.17 mmol), which was dissolved in toluene (2.5 mL) under a nitrogen atmosphere. Tetrakis (triphenylphosphine) palladium (0) (70 mg, 0.06 mmol) was added to the flask followed by more toluene (2.5 mL). Aqueous sodium carbonate (2.0 M, 2 mL, 4 mmol) was added, followed by a solution of 3-trifluoromethylphenyl boronic acid (489 mg, 2.57 mmol) in ethanol (2.5 mL). A nitrogen atmosphere was established by evacuating and refilling with nitrogen (3×), then the flask was sealed and heated in a 110° C. oil bath overnight. The resulting mixture was cooled to room temperature. Aqueous hydrogen peroxide solution (30%, 0.3 mL) was added and the mixture was stirred for 1 h. The reaction was then diluted with water (25 mL) and extracted with ethyl ether or EtOAc (3×75 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified on a Teledyne-Isco Combiflash machine (40 g column, hexanes→40% EtOAc/hexanes, gradient), to afford 628 mg (99%) of 5-(3-(trifluoromethyl)phenyl)-3,4-dihydronaphthalen-1(2H)-one.

Workup

  1. customby evacuating
  2. customthe flask was sealed
  3. temperatureThe resulting mixture was cooled to room temperature
  4. additionAqueous hydrogen peroxide solution (30%, 0.3 mL) was added
  5. additionThe reaction was then diluted with water (25 mL)
  6. extractionextracted with ethyl ether or EtOAc (3×75 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting crude residue was purified on a Teledyne-Isco Combiflash machine (40 g column, hexanes→40% EtOAc/hexanes, gradient)

Sources & evidence

ORD record
ord-c531b2544e5f45ffa06dd038d9f0071f
Source dataset
uspto-grants-2016_08
Patent number
US09415027B2

Reaction notes

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