Ethyl Acetate → 5,10,15,20-Tetrakis(2,6-dihydroxyphenyl)porphyrin

HRID 64518Notes

Reaction equation

HRID 64518 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.C(OCC)(=O)C>ClCCl>[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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 135542237HCID 135542237, compound

Product 1

HCID 1354931875,10,15,20-Tetrakis(2,6-dihydroxyphenyl)porphyrinYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of porphyrin 1 (400 mg, 0.47 mmol) in dry dichloromethane (25 mL) at −20° C. was added BBr3 (451 μL, 4.68 mmol). The resulting green solution was stirred for 12 hours at room temperature, then placed in ice water, ethyl acetate was added to the suspension and the mixture was washed with NaHCO3. The organic layer was separated, washed twice with water and then dried over anhydrous Na2SO4. The resulting solution was evaporated. The residue was purified by column chromatography (silica gel, 20:1 ethyl acetate/methanol) to yield porphyrin 2 as a purple powder (300 mg, 87%). 1H NMR (400 MHz, MeOD): δ 8.81 (s, 8H), 7.38 (t, J=8 Hz, 4H), 6.72 (d, J=8 Hz, 8H). HRESI-MS ([M+H]+) calcd for C44H31N4O8 743.2436, found 743.2136.

Workup

  1. washthe mixture was washed with NaHCO3
  2. customThe organic layer was separated
  3. washwashed twice with water
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe resulting solution was evaporated
  6. customThe residue was purified by column chromatography (silica gel, 20:1 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-301223ee350d4a129cb59d204f53cc81
Source dataset
uspto-grants-2016_09
Patent number
US09447511B2

Reaction notes

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