Potassium Bromide → 1,2-Bis(4-bromobenzoyl)-1-methoxyethane

HRID 1450527

Reaktionsgleichung

Reaktionsgleichung von HRID 1450527
Br[CH:2]([C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[CH:3](Br)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1.[CH3:23][O-:24].[Na+].[K+].[Br-]>CO>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([CH:3]([O:24][CH3:23])[CH2:2][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)=[O:12])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 253877Potassium BromideHCID 10942334Sodium MethoxideHCID 117313561,2-Dibromo-1,2-di(4-bromobenzoyl)ethane

Produkt 1

HCID 196934911,2-Bis(4-bromobenzoyl)-1-methoxyethane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 1,2-dibromo-1,2-di(4-bromobenzoyl) ethane (11.1 g, 0.02 mole) in 150 ml dry methanol was added a solution of sodium methoxide in methanol (0.92 g sodium in 50 ml methanol). The yellow brown mixture was refluxed for 1-1.5 hr. The solvent was removed by distillation, the residue was suspended in water and the mixture was extracted with 100 ml chloroform. The chloroform extract was washed with water, dried (Na2SO4) and concentrated. The residue obtained was titrated with dry methanol-ether (3:1) to yield off-white crystalline solid, 6.6 g (78%), mp 153°-154° C. IR (KBr): 3106, 3062, 2932, 1689, 1649, 1583, 1556, 1403, 1223, 1202, 1182, 1086, 1010, 1000, 857, 814, 738, 618, 472 cm-1. 1H (DMSO-d6 /40° C.): 7.95 (d, 2H, J=7.8), 7.77 (4H, J=8.8), 7.72 (d, 2H, J=7.8), 6.89 (s, 1H), 4.03 (s, 3H). 13C (DMSO-d6 /40° C.): 189.9, 187.2, 168.8, 139.9, 135.9, 133.1, 132.2, 131.8, 130.3, 128.1, 127.4, 98.6, 58.5. MS m/e 424 (M+).

Aufarbeitung

  1. temperatureThe yellow brown mixture was refluxed for 1-1.5 hr
  2. customThe solvent was removed by distillation
  3. extractionthe mixture was extracted with 100 ml chloroform
  4. extractionThe chloroform extract
  5. washwas washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customto yield off-white crystalline solid, 6.6 g (78%), mp 153°-154° C

Quellen und Nachweise

ORD-Eintrag
ord-d883378f2ca3411680f2aa82fe9aa8c6
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602172

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