| 100% |
With thionyl chloride at 20℃; for 6h; |
|
| 98% |
With tert.-butylnitrite at 40℃; for 48h; |
44
Add compound 1ar (0.5 mmol, 106.2 mg) and methanol containing 40 mol% tert-butyl nitrite to the reaction tube; then react for 48 hours at 40°C in air; after the reaction, add sodium thiosulfate and stir. After quenching, using a rotary evaporator to remove the solvent, adsorbing on silica gel, and finally performing column chromatography with a mixed solvent of ethyl acetate and petroleum ether to obtain the product 3ar with a yield of 98%. |
| 98% |
With tert.-butylnitrite at 40℃; for 48h; Green chemistry; |
|
| 97% |
With thionyl chloride at 0 - 20℃; for 3h; |
|
| 96% |
With toluene-4-sulfonic acid for 1h; Heating; |
|
| 96% |
With hydrogenchloride In water monomer for 1h; Reflux; Inert atmosphere; Schlenk technique; Glovebox; |
|
| 93% |
With sulfuric acid In methanol for 4h; Inert atmosphere; |
|
| 92% |
With sulfuric acid at 0℃; for 16h; Reflux; |
1.1 1. Preparation of methyl biphenyl-4-ylacetate, Intermediate B
1. Preparation of methyl biphenyl-4-ylacetate, Intermediate B A solution of biphenyl-4-ylacetic acid (10.0 g, 47.1 mmol) in MeOH (100 mL) was charged with sulfuric acid (10 mL) at 0°C. The reaction mixture was stirred to reflux for 16 h. The reaction mixture was concentrated under the reduced pressure, diluted with ice water (100 mL) and was extracted with MTBE (2 100 mL). The combined organic layers were washed with saturated NaHC03 solution (100 mL), water (100 mL) and brine (50 mL). The organic layers were dried over anhydrous Na2SC and were concentrated under reduced pressure to afford methyl biphenyl-4-ylacetate (Intermediate B, 9.80 g, 92%) as a colourless liquid. 1H NMR (CDCb): δ 7.49 - 7.44 (m, 4H), 7.35 - 7.23 (m, 5H), 3.60 (s, 3H), 3.56 (s, 2H). |
| 91% |
With thionyl chloride at 0℃; for 2h; Reflux; |
|
| 90% |
With sulfuric acid for 3h; Reflux; |
|
|
With sulfuric acid |
|
|
With dmap; triethylamine In dichloromethane at 20℃; for 0.5h; |
|
|
With thionyl chloride at 0℃; Reflux; |
|
|
With thionyl chloride at 0 - 20℃; for 6h; |
|
|
With acetyl chloride at 0 - 20℃; Inert atmosphere; |
Methyl 2-([l,l'-biphenyl]-4-yl)-2-diazoacetate (2c); In a flame dried round bottom flask, 2-([l,l'-biphenyl]-4-yl) acetic acid (50 mmol, 1 eq.) was dissolved in MeOH (50 mL) and cooled to 0 °C. Acetyl chloride (60 mmol, 1.2 eq.) was added drop wise at 0 °C. The resultant reaction mixture was stirred at rt for overnight. The reaction mixture was poured in to a separation funnel having ethyl ether and saturated NH4C1 solution. Extracted twice; combined organic layers were washed with brine, dried over MgS04 and concentrated in vacuo. The crude methyl acetate mixture was taken to next step without further purification. |
| 180.8 g |
With sulfuric acid for 1h; Reflux; |
3
To 1000 ml of a four-necked flask equipped with a reflux condenser, 500 g of methanol was charged,200 g concentrated sulfuric acid and 180 g of crude 4-biphenylacetic acid,The temperature was refluxed for 1 hour,Cooled to room temperature,Standing for 30 minutes,Separate the methanol-containing sulfuric acid layer for the next batch,Above the oil layer after washing under vacuum distillation,180.8 g of a 210 ° C to 216 ° C / 5 mmHg fraction was collected,Is methyl 4-biphenylacetate. |
|
With sulfuric acid for 2h; Reflux; |
|
|
With sulfuric acid for 6h; Reflux; |
|
|
With thionyl chloride at 90℃; for 3h; Inert atmosphere; Schlenk technique; |
|
|
With sulfuric acid for 6h; Reflux; |
|
|
With sulfuric acid In methanol for 5h; Reflux; |
|
|
With sulfuric acid for 6h; Reflux; |
|
|
With thionyl chloride at 0 - 20℃; for 3h; |
|
|
With thionyl chloride at 60℃; for 0.5h; Cooling with ice; |
|
|
With sulfuric acid for 6h; Reflux; Inert atmosphere; |
|
|
With sulfuric acid for 16h; Reflux; |
|
| 37.3 mg |
With diazomethyl-trimethyl-silane In toluene at 20℃; for 1h; |
|
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