Ethyl Acetate → HCID 21350138, compound

HRID 1820703Notes

Reaction equation

HRID 1820703 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[CH3:24].C(OCC)(=O)C>COCCOC.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.CCCCCCC>[F:23][C:21]1[CH:22]=[C:17]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:18]([CH3:24])=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 740162-Bromo-4-fluorotoluene

Product 1

HCID 21350138HCID 21350138, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8900HeptaneSolvent

Procedure

Potassium carbonate (659 mg, 4.27 mmol), phenylboronic acid (388 mg, 3.18 mmol), 2-bromo-4-fluorotoluene (0.20 mL, 1.59 mmol), and tetrakis(triphenylphosphine)palladium(0) (92 mg, 5mol %), in DME (3 mL) were sealed in a microwave vessel and heated at 80° C. for 1200s, then 120° C. for 1200s. Ethyl acetate (5 mL) was added and the reaction was filtered and concentrated in vacuo. The crude material was then purified by flash column chromatography on silica gel. Elution with 10:90 ethyl acetate:heptane afforded 3-fluoro-6-methylbiphenyl (253 mg, 1.36 mmol, 86%).

Workup

  1. custom120° C.
  2. filtrationthe reaction was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude material was then purified by flash column chromatography on silica gel
  5. washElution with 10:90 ethyl acetate

Sources & evidence

ORD record
ord-6711b2c59e91413297c03cdd652b4061
Source dataset
uspto-grants-2009_10
Patent number
US07605170B2

Reaction notes

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