반응 #1107971

반응 방정식

(i-PrO)3B

2-(4-bromo-2-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran

n-BuLi

(i-PrO)3B

→

6-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol

수율 73.9%

용매

THF

반응 조건

후처리

1. 1
   기타Reaction mixture
2. 2
   workup.ADDITIONwas then treated
3. 3
   workup.ADDITIONwas added via syringe
4. 4
   온도the reaction mixture was warmed to room temperature
5. 5
   기타before quenching
6. 6
   기타the reaction with equal volume of concentrated NH4Cl(aq) and EtOAc (1:1, 30 mL)
7. 7
   기타The layers were separated
8. 8
   추출the water phase was further extracted with equal volume of EtOAc before the organic layers
9. 9
   건조dried over anhydrous Na2SO4
10. 10
    여과filtered
11. 11
    기타The solvent was removed under reduced pressure
12. 12
    기타The residue was purified by silica gel column

실험 절차

A solution of 2-(4-bromo-2-fluoro-5-((tetrahydro-2H-pyran-2-yloxy)methyl)phenoxy)tetrahydro-2H-pyran (6.31 g, 16.2 mmol) in anhydrous THF (13.5 mL) was made before cooling the reaction mixture in a −78° C. bath. Reaction mixture was then treated, drop-wise, with n-BuLi (12.15 mL, 19.45 mmol) and allowed to stir for 1.0 hr before (i-PrO)3B (5.59 mL, 24.3 mmol) was added via syringe. After the addition of (i-PrO)3B, the reaction mixture was warmed to room temperature and allowed to stir for 2 hr before quenching the reaction with equal volume of concentrated NH4Cl(aq) and EtOAc (1:1, 30 mL). The layers were separated and the water phase was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 6-fluorobenzo[c][1,2]oxaborole-1,5(3H)-diol (2.01 g, 73.93%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 4.85 (s, 2H), 6.95 (d, J=5.4 Hz, 1H), 7.36 (d, J=8.1 Hz, 1H), 8.98 (s, 1H), 10.22 (s, 1H).

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