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288401-07-0

5'-CHLORO-2'-HYDROXY-4'-METHYL-3'-NITROACETOPHENONE synthesis

2synthesis methods
28480-70-8 Synthesis
5'-CHLORO-2'-HYDROXY-4'-METHYLACETOPHENONE

28480-70-8
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$18.00/5g

5'-CHLORO-2'-HYDROXY-4'-METHYL-3'-NITROACETOPHENONE

288401-07-0
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Yield:288401-07-0 62%

Reaction Conditions:

with sulfuric acid;sodium nitrite at 0; for 0.5 h;

Steps:

51.1 Step 1: 1- (5-chloro-2-hydroxy-4-methyl-3-nitrophenyl) ethan-1-one (51-1)

To a solution of 1- (5-chloro-2-hydroxy-4-methylphenyl) ethan-1-one (1 g, 5.42 mmol) in H 2SO 4 (5 mL) was added NaNO 2 (690 mg, 8.12 mmol) at 0 . The reaction mixture was stirred at 0 for 0.5 hr. The reaction mixture was poured into ice, the resulting aqueous layer was extracted with ethyl acetate (250 mL x 2) . The organic layer was washed with brine (100 mL) and dried over Na 2SO 4. The solvent was evaporated to dryness. The residue was purified with column chromatography on silica gel (petroleum ether: ethyl acetate =10: 1) to obtain the desired compound as yellow solid (770 mg in 62%yield) . 1H NMR (400 MHz, CDCl 3) δ 12.60 (s, 1H) , 7.84 (s, 1H) , 2.66 (s, 3H) , 2.38 (s, 3H) . MS (ESI) m/e (M+1) + 230.0.

References:

WO2018/103688,2018,A1 Location in patent:Paragraph 0530

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