(Bromomethyl)cyclobutane → 2-(3-(3-(Cyclobutylmethoxy)phenyl)propyl)isoindoline-1,3-dione

HRID 74356

Reaction equation

HRID 74356 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:5]=[CH:6][CH:7]=1.[CH:22]1([CH2:26]Br)[CH2:25][CH2:24][CH2:23]1>>[CH:22]1([CH2:26][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][N:11]3[C:19](=[O:20])[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]3=[O:21])[CH:5]=[CH:6][CH:7]=2)[CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 2734658(Bromomethyl)cyclobutaneHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Product 1

HCID 673169292-(3-(3-(Cyclobutylmethoxy)phenyl)propyl)isoindoline-1,3-dione

Procedure

Alkylation reaction of phenol 58 with cyclobutylmethyl bromide gave 2-(3-(3-(cyclobutylmethoxy)phenyl)propyl)isoindoline-1,3-dione as yellow oil. Yield (0.430 g, 34%): 1H NMR (400 MHz, CDCl3) δ 7.82-7.84 (m, 2H), 7.69-7.71 (m, 2H), 7.11-7.16 (m, 1H), 6.73-6.78 (m, 2H), 6.66 (dd, J=7.6, 2.4 Hz, 1H), 3.88 (d, J=6.4 Hz, 2H), 3.75 (t, J=7.2 Hz, 2H), 2.70-2.79 (m, 1H), 2.66 (t, J=8.0 Hz, 2H), 2.10-2.17 (m, 2H), 2.00-2.07 (m, 2H), 1.82-1.98 (m, 4H).

Sources & evidence

ORD record
ord-82055c7ab4a742ccb040dcd005d52371
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Linked notes

Loading…