Potassium Carbonate → HCID 21871140, compound

HRID 2403045Notes

Reaction equation

HRID 2403045 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](Br)[CH:6]=[CH:5]2.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([F:21])[C:19]=1[F:20].C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1>[F:13][C:14]1[CH:15]=[C:16]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[CH:3]=[C:2]([OH:1])[CH:11]=[CH:10]3)[CH:17]=[C:18]([F:21])[C:19]=1[F:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 21871140HCID 21871140, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A flame dried 500 ml round-bottomed flask with a magnetic stir bar, was charged with 6-hydroxy-2-bromonaphthalene (8.0 g, 35.89 mMol), 3,4,5-trifluorophenyl boronic acid (6.9 g, 39.5 mMol), 75 mL toluene, 2M K2CO3 (80 mL), Bu4NBr (50 mg) and the mixture flushed with argon for 10 min. [Pd(PPh3)4] (0.5 g) was added and the mixture heated under argon at ˜85° C. overnight, with vigorous stirring. After cooling to room temperature, 50 mL water was added, extracted with 3×25 mL ethyl acetate, the organic extracts dried over MgSO4, and the crude product was then crystallized from a mixture of hexane and few drops of methanol. Yield: 8 g (87%).

Workup

  1. customA flame dried 500 ml round-bottomed flask with a magnetic stir bar
  2. customthe mixture flushed with argon for 10 min. [Pd(PPh3)4] (0.5 g)
  3. additionwas added
  4. temperatureAfter cooling to room temperature
  5. addition50 mL water was added
  6. extractionextracted with 3×25 mL ethyl acetate
  7. dry with materialthe organic extracts dried over MgSO4
  8. customthe crude product was then crystallized from a mixture of hexane and few drops of methanol

Sources & evidence

ORD record
ord-7feeb0f6183749958a96e200c0918a6c
Source dataset
uspto-grants-2014_08
Patent number
US08801966B2

Reaction notes

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