Phthalimide → HCID 57608453, compound

HRID 1618442Notes

Reaction equation

HRID 1618442 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH2:10]O)[CH:5]=[CH:6][CH:7]=1.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12>>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH2:10][N:16]2[C:12](=[O:22])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:17])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6809PhthalimideHCID 57608491HCID 57608491, compound

Product 1

HCID 57608453HCID 57608453, compound

Procedure

Mitsunobu coupling of 2-(3-bromophenylthio)ethanol (125) with phthalimide according to the method used in Example 17, followed by flash chromatography (5-20% ethyl acetate/hexanes gradient) gave 2-(2-(3-bromophenylthio)ethyl)isoindoline-1,3-dione (126) as a white solid. Yield (4.04 g, 72%): 1H NMR (400 MHz, CDCl3) δ 7.77-7.84 (m, 2H), 7.66-7.72 (m, 2H), 7.50 (t, J=2.0 Hz, 1H), 7.30 (ddd, J=0.8, 1.6, 7.6 Hz, 1H), 7.19 (ddd, J=0.8, 1.6, 7.6 Hz, 1H), 7.07 (t, J=7.6 Hz, 1H), 3.93 (t, J=7.2 Hz, 2H), 3.22 (J=7.2 Hz, 2H).

Sources & evidence

ORD record
ord-55afa351b82e47e191f133507ba09b79
Source dataset
uspto-grants-2014_07
Patent number
US08766007B2

Reaction notes

Loading…