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With trichloroacetonitrile; triphenylphosphine In acetonitrile at 20℃; |
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With thionyl chloride for 1.5h; Heating; |
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With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; |
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With thionyl chloride |
V EXAMPLE V
EXAMPLE V 50g of 2-bromoisovaleric acid was mixed with 80 ml of thionylchloride and the mixture was refluxed for 4 hours to give 45.9g of 2-bromoisovaleryl chloride. (b.p. 68° - 70°C/29 mmHg) |
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With thionyl chloride for 2h; Heating; |
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With sulfuryl dichloride |
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With oxalyl dichloride In dichloromethane at 20℃; for 16h; |
17; 10
To a solution of 2-bromo-3 -methyl butanoic acid (1.07 g, 5.91 mmol) in anhydrous CH2Cl2 (10 mL), a droplet of DMF and oxalyl chloride (1.5 mL, 17 mmol) were added at room temperature under nitrogen atmosphere. After stirring for 16 h, the reaction mixture was concentrated under reduced pressure and azeotroped with toluene. To the obtained residue, 3-amino-5-bromobenzofuran-2-carboxamide (1, 186 mg, 0.73 mmol) and chloroform were added. The mixture was heated to 40 0C for 3 h. The mixture was poured over aqueous saturated NaHCO3 (120 mL) and the organic phase was separated. The aqueous layer was further extracted with CHCl3 (2x 80 mL) . The combined organic layers were dried over MgSO4, then concentrated in vacuo. After purification by flash chromatography (91 :8:1 dichloromethane/methanol/28% (w/w) ammonium hydroxide), the title compound was obtained as an oil (198 mg), 65% yield. 1H NMR (400 MHz, CDCl3) δ 10.64 (br s, IH), 8.66 (d, J= 3 Hz, IH), 7.56 (dd, J= 3, J= 9 Hz, IH), 7.31 (d, J= 9 Hz, IH), 6.41 (br s, IH), 5.80 (br s, IH), 4.37 (d, J= 6.5 Hz, IH), 2.46 (sept, J= 6.5 Hz, IH), 1.14 (dd, J= 3, J= 6.5 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 167.3, 162.6, 152.4, 133.0, 131.8, 129.7, 127.9, 123.4, 116.7, 113.4, 59.5, 33.1, 20.9, 19.5; MS (ESI+) for Ci4Hi4Br2N2O3: 419 (MH+). |
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With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 0 - 20℃; |
32.4 Production of 2-amino-6-isopropylphenol hydrobromide
Step 4 Production of 2-bromo-3-methylbutyryl chloride Chloroform (200 mL) was added to 2-bromo-3-methylbutyric acid (25 g), and oxalyl chloride (14.5 mL) and N,N-dimethylformamide (3 drops) were added under ice-cooling. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, and azeotroped with toluene to give the title compound as a yellow oil. |
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With oxalyl dichloride In chloroform at 1 - 40℃; |
6.1
step 1 Production of 2-bromo-3-methylbutyryl chloride 2-Bromo-3-methylbutyric acid (25 g) was dissolved in chloroform (200 mL), oxalyl chloride (14.5 mL) and N,N-dimethylformamide (three drops) were added. After stirring the mixture overnight at room temperature, the mixture was concentrated, and the residue was azeotroped with chloroform and toluene to give the title compound as a yellow oil. |
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With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Inert atmosphere; |
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With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; |
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With oxalyl dichloride at 60℃; for 2h; |
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With thionyl chloride for 2h; Reflux; |
4.1.1.1. 2-Bromohexanoyl chloride (36a).
General procedure: A flask was charged with2-bromohexanoic acid (1.95 g, 10 mmol) at 0 C and thionyl chloride (10 mL) was added dropwise. The mixture was stirred at rt for 10 min and then heated under reflux for 2 h. The excess thionylchloride was removed by distillation and the resulting acyl chloride was used without any further purification. |
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With thionyl chloride; N,N-dimethyl-formamide In toluene at 35 - 40℃; for 4h; Inert atmosphere; |
1.S1 S1: Synthesis of α-bromoisovaleryl chloride.
With a thermometer,Mechanical agitation,In the 2L four-neck bottle of the constant pressure dropping funnel device,Under nitrogen protection,Α- bromo-isovaleric acid was added 100g,Toluene 500ml and 0.1g N,N-dimethylformamide (DMF),Control at 35-40 ° C,69 g of thionyl chloride was added dropwise and stirring was continued for 4 hours.Until the reaction is complete, the tail gas is absorbed by the alkaline water. |
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With oxalyl dichloride; N,N-dimethyl-formamide In chloroform at 0 - 40℃; |
32.4
Step 4 Production of 2-bromo-3-methylbutyryl chloride Chloroform (200 mL) was added to 2-bromo-3-methylbutyric acid (25 g), and oxalyl chloride (14.5 mL) and N,N-dimethylformamide (3 drops) were added under ice-cooling. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, and azeotroped with toluene to give the title compound as a yellow oil. |
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