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

HRID 793

反応式

HRID 793 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-68a4112e542d4a8cb9aa4b70a263e0cb
出典データセット
uspto-grants-1998_03
特許番号
US05723288

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