Methanol → 5,6-Dibromo-4,7-dimethyl-1,4-epoxy-1,4-dihydronaphthalene

HRID 1060703

反応式

HRID 1060703 の反応式
Br[C:2]1[C:7]([CH3:8])=[C:6]([Br:9])[C:5]([Br:10])=[C:4]([CH3:11])[C:3]=1Br.[O:13]1C=[CH:16][CH:15]=[CH:14]1.[Li][CH2:19]CCC.CO>C1(C)C=CC=CC=1.O>[Br:10][C:5]1[C:6]([Br:9])=[C:7]([CH3:8])[CH:2]=[C:3]2[C:4]=1[C:11]1([CH3:19])[O:13][CH:14]2[CH:15]=[CH:16]1

参加物

7

反応物 4

HCID 887MethanolHCID 8029FuranHCID 31952Benzene, 1,2,4,5-tetrabromo-3,6-dimethyl-HCID 178418339Butyllithium

生成物 1

HCID 226789125,6-Dibromo-4,7-dimethyl-1,4-epoxy-1,4-dihydronaphthalene収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silica gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values.22

後処理

  1. temperatureto warm to rt
  2. waitAfter 3 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with Et2O
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-fd02ffed20e44a959ccb4cdc5ae1fffe
出典データセット
uspto-grants-2003_02
特許番号
US06525068B1

関連ノート

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