Potassium Carbonate → (E)-3-cyclohexyl-2-(3-fluoro-4-methanesulfonyl-phenyl)-prop-2-en-1-ol

HRID 2103629Notes

Reaction equation

HRID 2103629 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=1.[CH:13]1(/[CH:19]=[C:20](\B2OC(C)(C)C(C)(C)O2)/[CH2:21][OH:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)(C)C.O.C1(P([Pd-4](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)C=CC=CC=1>[CH:13]1(/[CH:19]=[C:20](\[C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=2)/[CH2:21][OH:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 459337204-Bromo-2-fluoro-1-(methylsulfonyl)benzeneHCID 67084598(E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 67084460(E)-3-cyclohexyl-2-(3-fluoro-4-methanesulfonyl-phenyl)-prop-2-en-1-olYield 88.6%

Reagents, catalysts & solvents 4

HCID 178420553HCID 178420553, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

Heat a mixture of 4-bromo-2-fluoro-l -methanesulfonyl-benzene (220 mg, 0.86 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (298 mg, 1.12 mmol), potassium carbonate (356 mg, 2.58 mmol) and tetrakis(triphenylphosphino)palladium(0) (99 mg, 86 μmol) in 40 mL toluene, 5 mL iso-propanol and 5 mL water to reflux for 2 h. After cooling to r.t. extract with ethyl acetate, wash the combined organic extracts with brine, dry them over sodium sulfate, filtrate and concentrate to obtain a brown oil. Purify the crude product by column chromatography, eluting with a gradient from 100:0 to 0:100 hexanes:ethyl acetate to obtain (E)-3-cyclohexyl-2-(3-fluoro-4-methanesulfonyl-phenyl)-prop-2-en-1-ol (238 mg) as a pale yellow oil. MS (m/e): 295 [(M−H2O)+H].

Workup

  1. temperatureHeat
  2. temperatureto reflux for 2 h
  3. extractionextract with ethyl acetate
  4. washwash the combined organic extracts with brine
  5. dry with materialdry them over sodium sulfate, filtrate
  6. concentrationconcentrate
  7. customto obtain a brown oil
  8. customPurify the crude product by column chromatography
  9. washeluting with a gradient from 100:0 to 0:100 hexanes

Sources & evidence

ORD record
ord-dd9550353fc04a1bb07200f65aadbac5
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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