4-BROMO-3'-METHYLBENZOPHENONE synthesis
- Product Name:4-BROMO-3'-METHYLBENZOPHENONE
- CAS Number:27428-61-1
- Molecular formula:C14H11BrO
- Molecular Weight:275.14
Yield:27428-61-1 61%
Reaction Conditions:
with copper(l) iodide;palladium(II) trifluoroacetate;triphenyl-arsane;norbornene;potassium carbonate;p-benzoquinone in toluene at 100; for 14 h;Sealed tube;Molecular sieve;
Steps:
2.4 General procedure of palladium and norbornene catalyzed ortho acylation reaction
General procedure: A flame-dried 4.0 mL vial was charged with Pd(TFA)2 (9.9 mg, 0.03 mmol, 10 mol%), benzoquinone (3.3mg, 0.03 mmol, 10 mol%), CuI (17.1 mg, 0.09 mmol, 30 mol%), AsPh3 (27.6 mg, 0.09 mmol, 30 mol%),arylboroxine (0.3 mmol, 1.0 equiv, based on monomer) and substituted benzoic anhydride (0.6 mmol, 2.0equiv). The vial was directly transferred into a nitrogen-filled glovebox without caps. Then, K2CO3 (6.2 mg,0.045 mmol, 15 mol%) and 4? molecular sieves (400 mg) were added. In another 4.0 mL vial, NBE (16.9mg, 0.18 mmol) was dissolved in 1.5 mL dry toluene. 0.5 mL of this NBE solution (5.64 mg, 0.06 mmol, 20mol%) was transferred into the reaction mixture, before another 3.5 mL dry toluene was added. The vialwas tightly sealed, transferred out of glovebox and stirred on a pie-block preheated to 100 oC for 14 hours.After completion of the reaction, the mixture was filtered through a thin pad of silica gel. The filter cakewas washed with ethyl acetate and the combined filtrate was concentrated. The residue was loaded to asmall amount of silica gel and then purified by flash column chromatography on silica gel to give thedesired ortho acylation product.
References:
Li, Renhe;Liu, Feipeng;Dong, Guangbin [Chem,2019,vol. 5,# 4,p. 929 - 939] Location in patent:supporting information
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