3-Bromo-4-(trifluoromethoxy)benzoic acid → 1261753-62-1

A mixture of 3-bromo-4-(trifluoromethoxy)benzoic acid (923 mg, 3.24 mmol) and PdCl2(dppf) (95 mg, 0.13 mmol) were stirred in 1,4-dioxane (9 mL) in a three necked flask under argon atmosphere (a condensor was added to the flask). Dimethylzinc in toluene (3.2 mL of 2.0 M, 6.4 mmol) was added very slowly (caution: the reaction was very exothermic) and the mixture was stirred at room temperature for 1 hour before it was heated at 70° C. for 18 h. The mixture was cooled to room temperature before it was charged with additional dioxane (9 mL) and PdCl2(dppf) (100 mg). The mixture was cooled to 0° C. before additional dimethyl zinc in toluene (3.0 mL, 2.0M) was added. The ice bath was removed and the mixture was heated at 70° C. overnight. The mixture was cooled to room temperature and was quenched with methanol (2 mL) very slowly. The solution was diluted with ethyl acetate and was washed with 1N HCl (3×). The organic layer was washed with brine, dried over sodium sulfate and evaporated to dryness to yield 3-methyl-4-(trifluoromethoxy)benzoic acid (56%).

1. additionwas added to the flask)
2. temperaturewas heated at 70° C. for 18 h
3. temperatureThe mixture was cooled to room temperature before it
4. additionwas added
5. customThe ice bath was removed
6. temperaturethe mixture was heated at 70° C. overnight
7. temperatureThe mixture was cooled to room temperature
8. customwas quenched with methanol (2 mL) very slowly
9. additionThe solution was diluted with ethyl acetate
10. washwas washed with 1N HCl (3×)
11. washThe organic layer was washed with brine
12. dry with materialdried over sodium sulfate
13. customevaporated to dryness

ORDレコード

ord-56550647249f42e18d8fe9bd0ea08940

出典データセット

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09365588B2