Реакция #168676

Уравнение реакции

EtOAc iso-hexane

Triethylborate

3-bromo-5-trifluoromethyl-pyridine

n-butyl lithium

HCl

→

title compound

5-(Trifluoromethyl)pyridin-3-ylboronic acid

Растворители

THF

Условия реакции

Обработка

1. 1
   Другоеthe temperature below −65° C
2. 2
   workup.ADDITIONOnce addition
3. 3
   Температураto warm slowly to room temperature
4. 4
   workup.STIRRINGthe reaction mixture stirred for 15 minutes
5. 5
   ДругоеThe layers are separated
6. 6
   Промывкаthe organic layer is washed with 1M HCl (200 ml)
7. 7
   Промывкаwashed with EtOAc (2×250 ml)
8. 8
   workup.ADDITIONThe pH of the aqueous phase is adjusted by the addition of 2M NaOH
9. 9
   Экстракцияextracted with EtOAc (2×250 ml)
10. 10
    КонцентрированиеConcentration in vacuo
11. 11
    Другоеaffords a solid, which

Методика

Triethylborate (24 ml, 139 mmol) is added to a solution of 3-bromo-5-trifluoromethyl-pyridine (30 g, 133 mmol) in THF (300 ml) and the resulting pale yellow solution is cooled to −78° C. A solution of 1.6 M n-butyl lithium in hexanes (97 ml, 139 mmol) is added via cannula dropwise over 40 minutes, keeping the temperature below −65° C. Once addition is complete, the reaction mixture is allowed to warm slowly to room temperature and stirred for 1 hour. 1M HCl (200 ml) is added and the reaction mixture stirred for 15 minutes. The layers are separated and the organic layer is washed with 1M HCl (200 ml). The aqueous layers are combined and washed with EtOAc (2×250 ml). The pH of the aqueous phase is adjusted by the addition of 2M NaOH, and extracted with EtOAc (2×250 ml). Concentration in vacuo affords a solid, which is recyrstallised from EtOAc/iso-hexane to yield the title compound as a yellow solid [M+H]+ 192.

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