(2-Fluoro-4,5-dihydroxy-phenyl)-morpholin-4-yl-methanone → [2,2-Bis-(2-chloro-phenyl)-6-fluoro-benzo[1,3]dioxol-5-yl]-morpholin-4-yl-methanone

HRID 2184136Notes

Reaction equation

HRID 2184136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])(Cl)Cl.[F:18][C:19]1[CH:24]=[C:23]([OH:25])[C:22]([OH:26])=[CH:21][C:20]=1[C:27]([N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[O:28]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[O:25][C:23]2[CH:24]=[C:19]([F:18])[C:20]([C:27]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[O:28])=[CH:21][C:22]=2[O:26]1

Participants

3

Reactant 2

HCID 21865388(2-Fluoro-4,5-dihydroxy-phenyl)-morpholin-4-yl-methanoneHCID 22474994Bis-(2-chlorophenyl)dichloromethane

Product 1

HCID 22475065[2,2-Bis-(2-chloro-phenyl)-6-fluoro-benzo[1,3]dioxol-5-yl]-morpholin-4-yl-methanoneYield 4.5%

Conditions

Temperature
150 °C

Procedure

A mixture of bis-(2-chlorophenyl)dichloromethane (Example 182, 258 mg, 0.84 mmol, 2.6 eq.) and (2-fluoro-4,5-dihydroxy-phenyl)-morpholin-4-yl-methanone (Example 87b, 72 mg, 0.32 mmol) were heated 5 h at 150° C. in a sealed glass tube. Purification by flash chromatography afforded the title compound (6.8 mg, 4.5%) as an off-white solid, m.p.: 98° C.

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-25d12f71fc984de5bb1845649b9378bd
Source dataset
uspto-grants-2005_05
Patent number
US06900227B2

Reaction notes

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