1,1-Dichloroethane → HCID 14234687, compound

Temperature

80 °C

A solution of 6-amino-m-cresol (1.0 g, 8.1 mmol) in 10 mL of dry dichloroethane is add to a prestirred solution of 2-bromo-3-methylbutyic acid (1.61 g, 8.9 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.71 g, 8.9 mmol) in 20 mL of dry dichloroethane. The reaction stirred overnight before quenching with water (50 mL) and extracting with chlrorform (3×50 mL). The combined organic layers were dried with sodium sulfate, filtered and excess solvent removed on the rotary evaporator. The crude solid was then dissolved in 15 mL of dry DMF and treated with cesium carbonate (5.86 g, 18 mmol) and heated to 80° C. for 6 hours. The reaction mixture was then cooled and quenched with 50 mL of water and extracted with chloroform (3×50 mL). The combined organic layers were dried with sodium sulfate, filtered and excess solvent removed on the rotary evaporator. The crude product was then purified using flash chromatography (10% EtOAc/hexanes) to yield 1.08 g (65%) of product as an off white solid. MS (electrospray): mass calculated for C12H15NO2, 205.11; m/z found 206.1 [M+H]+.

1. custombefore quenching with water (50 mL)
2. extractionextracting with chlrorform (3×50 mL)
3. dry with materialThe combined organic layers were dried with sodium sulfate
4. filtrationfiltered
5. customexcess solvent removed on the rotary evaporator
6. dissolutionThe crude solid was then dissolved in 15 mL of dry DMF
7. temperatureThe reaction mixture was then cooled
8. customquenched with 50 mL of water
9. extractionextracted with chloroform (3×50 mL)
10. dry with materialThe combined organic layers were dried with sodium sulfate
11. filtrationfiltered
12. customexcess solvent removed on the rotary evaporator
13. customThe crude product was then purified

ORD record

ord-ecbb77f8514b450a8a5515be6f8b5ad0

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723326B2