1-Bromomethyl-2,6-dichlorobenzene → Phthalimide

HRID 1014619Notes

Reaction equation

HRID 1014619 reaction equation
OC1C=C(CCC[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])C=CC=1.ClC1C=CC=C(Cl)C=1CBr>>[C:12]1(=[O:21])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19](=[O:20])[NH:11]1

Participants

3

Reactant 2

HCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

Product 1

HCID 6809Phthalimide

Procedure

Alkylation reaction of phenol 58 with 2,6-dichlorobenzylbromide gave 2-(3-3-(2,6-dichlorobenzyloxy)phenyl)propyl)isoindoline-1,3-dione as yellow oil. Yield (0.780 g, 51%): 1H NMR (400 MHz, CDCl3) δ 7.82-7.85 (m, 2H), 7.69-7.72 (m, 2H), 7.35-7.38 (m, 1H), 6.86-6.79 (m, 2H), 6.81 (s, 1H), 6.80 (dd, J=8.2, 2.4 Hz, 1H), 5.25 (s, 2H), 3.76 (t, J=6.2 Hz, 2H), 2.68 (t, J=7.6 Hz, 2H), 2.00-2.09 (m, 2H).

Sources & evidence

ORD record
ord-110820ee85984de5b22613b42d59a579
Source dataset
uspto-grants-2011_07
Patent number
US07982071B2

Reaction notes

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