4-Chloro-3-methylphenol synthesis
- Product Name:4-Chloro-3-methylphenol
- CAS Number:59-50-7
- Molecular formula:C7H7ClO
- Molecular Weight:142.58
108-39-4
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Yield:59-50-7 98.3%
Reaction Conditions:
with N-chloro-N-(phenylsulfonyl)benzenesulfonamide in acetonitrile at 20 - 25; for 0.166667 h;Green chemistry;
Steps:
General procedure for the monochlorination reaction
General procedure: To a solution of 4-nitroaniline, 1a (0.99 g, 7.2 mmol) in 7 mL specially dried MeCN was added N-chloro-N-(phenylsulfonyl)benzene sulfonamide (2.4 g, 7.2 mmol) in a 25 mL round bottom flask. The reaction mixture was stirred for 10-15 minutes at 20-25 °C (0 °C for 1-methyl-1H-imidazole, and N-methylindole), monitored by GC. After completion of the reaction, MeCN was distilled under vacuum at 40-45 °C. The residue was treated with 20 mL mixture of MDC and water, stirred the mixture for 10-15 minutes; MDC layer was separated and washed with 5 % sodium bicarbonate solution, after separation MDC layer was dried over sodium sulfate and evaporated under vacuum to obtain 2-chloro-4-nitroaniline, 2a, 1.22 g (98.5 % yield, 98.9 % purity) as a yellow powder.
References:
Misal, Balu;Palav, Amey;Ganwir, Prerna;Chaturbhuj, Ganesh [Tetrahedron Letters,2021,vol. 63,art. no. 152689] Location in patent:supporting information
13334-71-9
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84196-13-4
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108-39-4
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59-50-7
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615-74-7
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608-26-4
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59-50-7
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