p-Bromoacetophenone → 4-Acetylbiphenyl

HRID 1242824Notes

Reaction equation

HRID 1242824 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CCOCC.CC1C=CC=CC=1C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 7466p-BromoacetophenoneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 66827Phenylboronic Acid

Product 1

HCID 71134-AcetylbiphenylYield 101.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

Compound 5 (30 mg, 2 μmol Pd), 1-(4-bromophenyl)ethan-1-one (0.20 g, 1 mmol), phenylboronic acid (0.15 g, 1.2 mmol), potassium carbonate (0.21 g, 1.5 mmol), and o-xylene (3 mL) were sequentially added to a 15 mL septum-sealed test tube under protection of nitrogen. The mixture was then heated at 130° C. for 5 h. After it was cooled to the room temperature, 8 mL of anhydrous ether was added to precipitate compound 5. The mixture was centrifuged and f the upper liquid layer was transferred via a syringe into a 20 mL round-bottom flask. Repeated the above precipitation procedure once. The combined liquid layer was concentrated under reduced pressure to give an oily residue. A saturated ammonium chloride solution (5 mL) was then added. The resulting mixture was extracted by ethyl acetate (10 mL×3), dried over anhydrous magnesium sulfate, filtrated, and concentrated to give a crude product. The crude product was further purified by column chromatography (silica gel, hexane/ethyl acetate=4/1) to give 0.20 g (99% yield) of 4-acetylbiphenyl. 1H NMR (300 MHz, DMSO-d6) δ 2.61 (s, 3H), 7.42–7.44 (m, 1H), 7.48–7.51 (m, 2H), 7.73 (d, J=8.5 Hz, 2H), 7.81 (d, J=8.5 Hz, 2H), 7.69 (d, J=8.5 Hz, 2H) ppm.

Workup

  1. customseptum-sealed test tube under protection of nitrogen
  2. additionwas added
  3. customto precipitate compound 5
  4. customf the upper liquid layer was transferred via a syringe into a 20 mL round-bottom flask
  5. customthe above precipitation procedure once
  6. concentrationThe combined liquid layer was concentrated under reduced pressure
  7. customto give an oily residue
  8. extractionThe resulting mixture was extracted by ethyl acetate (10 mL×3)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltrated
  11. concentrationconcentrated
  12. customto give a crude product
  13. customThe crude product was further purified by column chromatography (silica gel, hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-f6c347528bed4310b53baffeabe63d8c
Source dataset
uspto-grants-2006_10
Patent number
US07115762B2

Reaction notes

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