3-Chlorophenol → HCID 58872535, compound

HRID 645104Notes

Reaction equation

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

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-3bdce8feb9844373a9b480a33e81d32b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700641B2

Reaction notes

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