Potassium Carbonate → Ethyl acetate hexane

HRID 511948Notes

Reaction equation

HRID 511948 reaction equation
Br[C:2]1[CH:11]=[CH:10]C=C2[C:3]=1[CH:4]=[CH:5]C=[C:7]2[CH2:12][OH:13].CC1C=C(C(F)(F)F)C=CC=1B(O)O.C([O-])([O-])=O.[K+].[K+].[O:34]1CCO[CH2:36][CH2:35]1>CCOC(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>[CH3:36][CH2:35][O:34][C:12]([CH3:7])=[O:13].[CH3:10][CH2:11][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 18963829(5-Bromonaphthalen-1-yl)methanolHCID 445581522-Methyl-4-(trifluoromethyl)benzeneboronic acid

Product 1

HCID 21226206Ethyl acetate hexaneYield 95%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(5-Bromonaphthalen-1-yl)methanol (165 mg), 2-methyl-4-trifluoromethylphenylboronic acid (170 mg, 1.2 eq.), Pd(PPh3)4 (80 mg, 0.1 eq.), and K2CO3 (288 mg, 3 eq.) were combined in a flask with 5 mL dioxane and 2.5 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. overnight. Solution was cooled to room temperature then diluted with EtOAc and washed with saturated NaHCO3. The organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 30% EtOAc/hexane yielding product as a yellow oil (208 mg, 95% yield). 1H NMR (400 MHz) (CDCl3) δ 8.24 (d, J=8 Hz, 1H), 7.65-7.64 (m, 1H), 7.63-7.56 (m, 2H), 7.40-7.36 (m, 5H), 5.23 (s, 2H), 2.10 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ144.16, 139.06, 137.81, 136.68, 131.92, 131.42, 130.74, 126.63, 126.51, 126.20, 125.82, 125.56, 123.73, 122.52, 122.48, 63.84, 20.06.

Workup

  1. customdegassed
  2. customReaction mixture
  3. temperatureSolution was cooled to room temperature
  4. washwashed with saturated NaHCO3
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ebfb8f235d1545b38475d54875ec45a0
Source dataset
uspto-grants-2015_08
Patent number
US09102617B2

Reaction notes

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