3-Chlorophenol → HCID 58872535, compound

HRID 545779Notes

Reaction equation

BrC1C=CC=C2C=1C(=O)C(=O)N2CCCCC.[O:18]=[C:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]1[CH2:29][C:30]([O:32][CH3:33])=[O:31].O1C2C=CC(O)=CC=2OC1.[Cl:44][C:45]1[CH:46]=[C:47]([OH:51])[CH:48]=[CH:49][CH:50]=1>>[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([C:27]2([OH:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[C:19]2=[O:18])=[C:47]([OH:51])[CH:46]=1

Participants

Reactant 4

HCID 79333-Chlorophenol

HCID 68289Sesamol

HCID 1902088HCID 1902088, compound

HCID 284924584-bromo-1-pentyl-1H-indole-2,3-dione

Product 1

HCID 58872535HCID 58872535, compound

Procedure

Following the procedure as described in PREPARATION 1C, and making non-critical variations to replace 4-bromo-1-pentyl-1H-indole-2,3-dione with methyl (2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate, and 1,3-benzodioxol-5-ol with 3-chlorophenol, the title compound was obtained (29%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 9.10 (s, 1H), 7.48 (d, 1H), 7.38 (t, 1H), 7.19 (t, 1H), 7.01 (br, 1H), 6.80-6.64 (m, 3H), 5.28 (br s, 1H), 4.51 (d, 1H), 4.44 (d, 1H), 3.75 (s, 3H); MS (ES+) m/z 370.5 (M+23), 372.4 (M+23).

Sources & evidence

ORD record: ord-15eb1dde8f184c6889b740ab27807254
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935721B2

Reaction notes

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