Boron tribromide → 5,10,15,20-Tetrakis(2,6-dihydroxyphenyl)porphyrin

HRID 1613863Notes

Reaction equation

HRID 1613863 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[C:11]1[C:12]2[NH:16][C:15]([C:17]([C:55]3[C:60]([O:61]C)=[CH:59][CH:58]=[CH:57][C:56]=3[O:63]C)=[C:18]3[N:54]=[C:21]([C:22]([C:44]4[C:49]([O:50]C)=[CH:48][CH:47]=[CH:46][C:45]=4[O:52]C)=[C:23]4[NH:43][C:26](=[C:27]([C:33]5[C:38]([O:39]C)=[CH:37][CH:36]=[CH:35][C:34]=5[O:41]C)[C:28]5[CH:29]=[CH:30][C:31]=1[N:32]=5)[CH:25]=[CH:24]4)[CH:20]=[CH:19]3)=[CH:14][CH:13]=2.B(Br)(Br)Br>ClCCl.C(Cl)(Cl)Cl.O1CCCC1>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[C:4]=1[C:11]1[C:12]2[NH:16][C:15]([C:17]([C:55]3[C:56]([OH:63])=[CH:57][CH:58]=[CH:59][C:60]=3[OH:61])=[C:18]3[N:54]=[C:21]([C:22]([C:44]4[C:49]([OH:50])=[CH:48][CH:47]=[CH:46][C:45]=4[OH:52])=[C:23]4[NH:43][C:26](=[C:27]([C:33]5[C:34]([OH:41])=[CH:35][CH:36]=[CH:37][C:38]=5[OH:39])[C:28]5[CH:29]=[CH:30][C:31]=1[N:32]=5)[CH:25]=[CH:24]4)[CH:20]=[CH:19]3)=[CH:14][CH:13]=2

Participants

6

Reactant 2

HCID 25134Boron tribromideHCID 135542237HCID 135542237, compound

Product 1

HCID 1354931875,10,15,20-Tetrakis(2,6-dihydroxyphenyl)porphyrin

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

As the solvent, acetic acid, propionic acid, butyric acid or the like is usable. The reaction temperature can be controlled by considering the kind of the solvent and the other conditions, usually a temperature of 80°-120° C. is selected. The reaction time is 5-12 hours, preferably 5-8 hours. After such condensation of these compounds, the tarry reaction mixture obtained by filtrating the reaction solution is purified by, for example, silica gel chromatography or the like to obtain 5,10,15,20-tetra(2',6'-dimethoxyphenyl)porphyrin. Then, 5,10,15,20-tetra(2',6'-dimethoxyphenyl)porphyrin is dissolved in a suitable dry solvent (dichloromethane, chloroform, tetrahydrofuran or the like), cooled in an ice-water bath 40 times or more of the molar quantity of boron tribromide is added and the mixture is stirred at room temperature for 10-24 hours. The reaction solution is poured dropwise into ice water, the solution is extracted by an organic solvent such as ethyl acetate, the organic layer is evaporated to dryness, and the solid is purified by silica gel chromatography to obtain 5,10,15,20-tetra(2',6'-dihydroxyphenyl)porphyrin (in the above process, the compound represented by H2T2,6-OH PP).

Workup

  1. temperaturethe like), cooled in an ice-water bath 40 times
  2. extractionthe solution is extracted by an organic solvent such as ethyl acetate
  3. customthe organic layer is evaporated to dryness
  4. customthe solid is purified by silica gel chromatography

Sources & evidence

ORD record
ord-5dae8d8f1e7940b6a5d696b036c756cc
Source dataset
uspto-grants-1993_03
Patent number
US05194603

Reaction notes

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