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

HRID 1837671

反応式

HRID 1837671 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 silca 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-c4cb626f255c44199db047776b7234b2
出典データセット
uspto-grants-2004_08
特許番号
US06784210B2

関連ノート

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