4-Chlorotoluene → 4-Methylbiphenyl

HRID 1014780Notes

Reaction equation

HRID 1014780 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13]C=[CH:11][CH:10]=1.[F-].[Cs+].O1CCOC[CH2:21]1>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH3:21][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 78104-ChlorotolueneHCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 66827Phenylboronic Acid

Product 1

HCID 125664-MethylbiphenylYield 56%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1317290462-Diphenylphosphino-dimethylaminoferroceneCatalyst

Procedure

According to General Procedure A, a mixture of 4-chlorotoluene (59 μL, 0.50 mmol), phenylboronic acid (91 mg, 0.75 mmol), CsF (228 mg, 1.50 mmol), Pd(OAc)2 (2 mg, 0.01 mmol) and 12f (8 mg, 0.02 mmol) in 1,4-dioxane (2.5 mL) was heated to reflux, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (1% Et2O in hexane silica gel) gave 51f (47 mg, 56%) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 7.59 (d, 2H, J=7.8 Hz), 7.51 (d, 2H, J=7.8 Hz), 7.44 (d, 2H, J=7.8 Hz), 7.35-7.24 (m, 3H), 2.41 (s, 3H); 13C NMR (75.5 MHz, CDCl3) δ 141.1, 138.3, 137.0, 129.5, 128.7, 127.0, 126.9, 21.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. customEvaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (1% Et2O in hexane silica gel)

Sources & evidence

ORD record
ord-cce08fa6e49944859ded9f9e25b8201d
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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