Phosphorus tribromide → 2-Bromomethyl-anthraquinone

HRID 266031Notes

Reaction equation

HRID 266031 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[CH:20]=[CH:19][C:18]2[C:17](=[O:21])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:22])[C:9]=2[CH:8]=1>O1CCCC1>[Br:2][CH2:6][C:7]1[CH:20]=[CH:19][C:18]2[C:17](=[O:21])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:22])[C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 870142-(Hydroxymethyl)anthraquinone

Product 1

HCID 3444522-Bromomethyl-anthraquinoneYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of PBr3 (82 mg, 302 μmole) in 5 mL of tetrahydrofuran (THF) was placed in ice bath. 2-Hydroxymethylanthraquinone (100 mg, 421 μmole) obtained from Aldrich Chemical Co., St. Louis, Miss., in 10 mL of THF was added to the mixture slowly over 10 minutes. After 1 hour at 0° C., the reaction temperature was raised to room temperature and the mixture was stirred for 48 hours. The mixture was evaporated and then redissolved in ethyl acetate for H2O extraction. The organic layer was dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. 2-Bromomethylanthraquinone was purified by flash silica column chromatography (Yield=52%). 1H NMR (300 MHz, CDCl3) δ 8.24 (2H, m), 8.14 (1H, s), 8.01(1H,d), 7.70 (1H, d), 7.57 (2H, m), 4.68 (2H, s).

Workup

  1. customThe mixture was evaporated
  2. dissolutionredissolved in ethyl acetate for H2O extraction
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. custom2-Bromomethylanthraquinone was purified by flash silica column chromatography (Yield=52%)

Sources & evidence

ORD record
ord-dbf38bf8d71d4307a1ff9f46b056bea1
Source dataset
uspto-grants-1997_07
Patent number
US05650399

Reaction notes

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