3-Bromophenol → HCID 68598646, compound

HRID 2385123Notes

Reaction equation

HRID 2385123 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:2]1=2.BrC1C=C(O)C=CC=1.[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][N:27]1[C:35]2[CH:34]=[C:33]3[O:36][CH2:37][CH2:38][O:39][C:32]3=[CH:31][C:30]=2[C:29](=[O:40])[C:28]1=[O:41].FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[OH:40][C:29]1([C:9]2[C:8]([OH:11])=[CH:7][C:3]3[O:4][CH2:5][CH2:6][O:1][C:2]=3[CH:10]=2)[C:30]2[CH:31]=[C:32]3[O:39][CH2:38][CH2:37][O:36][C:33]3=[CH:34][C:35]=2[N:27]([CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH3:20])[C:28]1=[O:41]

Participants

5

Reactant 4

HCID 115633-BromophenolHCID 91152732,3-Dihydro-1,4-benzodioxin-6-olHCID 673564881-((5-(Trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dioneHCID 68601607HCID 68601607, compound

Product 1

HCID 68598646HCID 68598646, compound

Procedure

Following the procedure as described in PREPARATION 2A and making non-critical variations using 2,3-dihydrobenzo[b][1,4]dioxin-6-ol to replace 3-bromophenol, and 6-[2-(2-methoxyethoxy)ethyl]-2,3-dihydro-6H-[1,4]dioxino[2,3-f]indole-7,8-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 8-hydroxy-8-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-6-[2-(2-methoxyethoxy)ethyl]-2,3,6,8-tetrahydro-7H-[1,4]dioxino[2,3-f]indol-7-one was obtained (19%): MS (ES+) m/z 441.9 (M−17).

Sources & evidence

ORD record
ord-cf81489d8c994cc3a8f717864cc7142e
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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