반응 #1004053

반응 방정식

HCl

butyl lithium

1-bromo-2-(1-ethoxy-ethoxymethyl)-4-fluoro-benzene

trimethyl borate

→

title compound

수율 70.9%

5-Fluoro-3H-benzo[c][1,2]oxaborol-1-ol

수율 70.9%

용매

THF

반응 조건

후처리

1. 1
   기타dropwise at −78° C
2. 2
   workup.ADDITIONUpon complete addition
3. 3
   기타the reaction at −78° C. for 10 minutes
4. 4
   기타the reaction to room temperature
5. 5
   workup.ADDITIONPour
6. 6
   workup.STIRRINGstir for 1 hour
7. 7
   추출Extract the biphasic mixture with ether three times
8. 8
   건조Dry the combined organic layers with sodium sulfate
9. 9
   여과filter
10. 10
    농축concentrate in vacuo
11. 11
    기타Triturate the oily residue with cold hexanes

실험 절차

Dissolve 1-bromo-2-(1-ethoxy-ethoxymethyl)-4-fluoro-benzene(5.4 g, 19.5 mmol) in dry THF (100 mL) and cool to −78° C. under nitrogen. Add butyl lithium (2.5M in Hexanes, 10.2 mL, 25.4 mmol) dropwise at −78° C. Upon complete addition, stir the reaction at −78° C. for 10 minutes and then add trimethyl borate (4.4 mL, 39 mmol) and warm the reaction to room temperature. Pour the reaction into 1N HCl (100 mL) and stir for 1 hour. Extract the biphasic mixture with ether three times. Dry the combined organic layers with sodium sulfate, filter and concentrate in vacuo. Triturate the oily residue with cold hexanes to yield 2.1 g (70%) of the title compound as a white solid. 1H NMR (d6-DMSO) 9.18 (s, 1H), 7.70 (dd, J=8.2, 5.8 Hz, 1H), 7.20 (dd, J=9.5, 2.7 Hz, 1H), 7.11 (m, 1H), 4.92 (s, 1H).

출처