4-Bromobenzophenone → 4-(2-Methylphenyl)benzophenone

HRID 412795Notes

Reaction equation

HRID 412795 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.[F-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[CH3:25][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 70304-BromobenzophenoneHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 185393294-(2-Methylphenyl)benzophenoneYield 98%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

A 4 ml vial was charged with 4-bromobenzophenone (268 mg, 1.03 mmol), o-tolylboronic acid (152 mg, 1.12 mmol), KF (116 mg, 2.00 mmol), Pd(dba)2 (5.8 mg, 1 mol %), and Ph5FcP(t-Bu)2 (7.1 mg, 2 mol %). Anhydrous toluene (2 ml) was added to the mixture, and the vial was sealed with a cap containing PTFE septum and removed from the drybox. The reaction solution was stirred at room temperature for 18 h. After the starting aryl halide was consumed, the reaction solution was directly absorbed onto silica gel and the coupling product was isolated by eluting with hexane/ethyl acetate to give 275 mg (98%) of 4-(2-methylphenyl)benzophenone as a solid:

Workup

  1. customthe vial was sealed with a cap
  2. customremoved from the drybox
  3. customAfter the starting aryl halide was consumed
  4. customthe reaction solution was directly absorbed onto silica gel
  5. customthe coupling product was isolated
  6. washby eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-3a29ec8455554c7cb00aa47a732f036b
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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