4-Bromophenol → 3-(5-bromo-2-hydroxyphenyl)-1-(diphenylmethyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one

HRID 425585Notes

Reaction equation

[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[C:9]2=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1C2C=CC(O)=CC=2OC1.[Br:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1>>[Br:35][C:36]1[CH:37]=[CH:38][C:39]([OH:42])=[C:40]([C:10]2([OH:17])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:9]2=[O:18])[CH:41]=1

Participants

Reactant 3

HCID 78084-Bromophenol

HCID 68289Sesamol

HCID 19692771-(diphenylmethyl)-1H-indole-2,3-dione

Product 1

HCID 120043353-(5-bromo-2-hydroxyphenyl)-1-(diphenylmethyl)-3-hydroxy-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2B, and making non-critical variations to replace1-(2-cyclopropylethyl)-1H-indole-2,3-dione with 1-(diphenylmethyl)-1H-indole-2,3-dione, and 1,3-benzodioxol-5-ol with 4-bromophenol, the title compound was obtained (90%) as an orange solid: MS (ES+) m/z 486.2 (M+1), 488.2 (M+1).

Sources & evidence

ORD record: ord-7eb0ee6a200a48f4ae0910f45e27bf76
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106087B2

Reaction notes

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