4-Bromoaniline → HCID 178449870、化合物

温度

0 °C

To an oven dried, N2 purged 250 mL round bottom flask attached with addition funnel was added 4-bromoaniline (7.31 g, 42.5 mmol) and anhydrous toluene (40 mL). To the reaction solution at 0° C. was added a 2.0 M Me3Al (32 mL, 1.5 molar equiv) solution. The reaction solution was stirred at 0° C. for 30 min, then a solution of 2-(2-fluorophenyl)-2-methylpropanenitrile (7.62 g, 46.7 mmol) in toluene (25 mL) was added to the reaction flask. The reaction solution was allowed to stir at 90° C. for 5 hr. The cooled reaction solution was quenched with an aq sodium potassium tartrate solution. After standing 20 min, the organic phase was partitioned and washed with sodium potassium tartrate solution. The organic solution was extracted with 1N aq HCl (100 mL×3). The combined aq HCl solution was neutralized by addition of 1N aq NaOH and extracted with dichloromethane (200 mL×2). The dichloromethane product solution was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound (5.5 g, 39% yield). GCMS m/z=334, 336 [M]+.

1. customTo an oven dried
2. customN2 purged 250 mL round bottom flask
3. additionattached with addition funnel
4. stirringto stir at 90° C. for 5 hr
5. customThe cooled reaction solution
6. customwas quenched with an aq sodium potassium tartrate solution
7. waitAfter standing 20 min
8. customthe organic phase was partitioned
9. washwashed with sodium potassium tartrate solution
10. extractionThe organic solution was extracted with 1N aq HCl (100 mL×3)
11. additionThe combined aq HCl solution was neutralized by addition of 1N aq NaOH
12. extractionextracted with dichloromethane (200 mL×2)
13. dry with materialThe dichloromethane product solution was dried over Na2SO4
14. filtrationfiltered
15. concentrationconcentrated in vacuo

ORDレコード

ord-ac6d2887a2ff4b399e550849d961e619

出典データセット

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08618154B2