ST4026352 → 1-(4-Hydroxybenzoyl)-3-(4-methoxybenzoyl)benzene

HRID 333205Notes

Reaction equation

HRID 333205 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:24])[C:16]3[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=3)[CH:10]=2)=[O:8])=[CH:5][CH:4]=1.CSC.B(F)(F)F>ClCCl>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([C:7](=[O:8])[C:6]3[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:10]=2)=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 344097ST4026352HCID 11137191Trifluoroborane-methyl sulfide

Product 1

HCID 867014251-(4-Hydroxybenzoyl)-3-(4-methoxybenzoyl)benzeneYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well-stirred solution of 1,3-bis-(4-methoxybenzoyl)benzene 14 (700 mg, 2.02 mmol) in dichloromethane (25 mL) was added boron trifluoride dimethyl sulfide complex (BF3.SMe2, 10 mL). The reaction was stirred for 16 h at room temperature, and then quenched with water, and extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified using flash chromatography (silica gel, hexanes:ethyl acetate, 50:50) to afford the pure 1-(4-hydroxybenzoyl)-3-(4-methoxybenzoyl)benzene 16 (0.2 g, 0.60 mmol) as a white solid in a 30% yield; 1H NMR (500 MHz, Acetone-d6): δ 9.19 (s, OH), 7.89 (dt, J=2 Hz, 0.5 Hz, 1H, ArH), 7.85 (dd, J=7.5 Hz, 1.5 Hz, 2H, ArH), 7.72 (ddd, J=10.0 Hz, 5.0 Hz, 3.0 Hz, 2H, ArH), 7.66 (ddd, J=9.5 Hz, 5.0 Hz, 3.0 Hz, 2H, ArH), 7.59 (td, J=7.5 Hz, 0.5 Hz, 1H, ArH), 6.96 (ddd, J=9.5 Hz, 4.5 Hz, 2.5 Hz, 2H, ArH), 6.86 (ddd, J=9.5 Hz, 5.0 Hz, 3.0 Hz, 2H, ArH), 3.78 (s, 3H, OCH3); 13C NMR (125 MHz, Acetone-d6): δ 193.70, 193.56, 163.61, 161.941, 138.58, 138.35, 132.62, 132.41, 132.30, 130.16, 129.67, 128.75, 128.56, 115.25, 113.78, 55.12.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-6b702937c490447296023dafec9c2463
Source dataset
uspto-grants-2014_11
Patent number
US08877967B2

Reaction notes

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