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

HRID 234115

Reaction equation

HRID 234115 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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 (Na2S04) 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+).

Workup

  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. customdried (Na2S04)
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customto yield off-white crystalline solid, 6.6 g (78%), mp 153°-154° C

Sources & evidence

ORD record
ord-c95f7223b74349748d230c53fe8cd9cf
Source dataset
uspto-grants-1997_01
Patent number
US05594138

Linked notes

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