Bromine → 4-bromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7821

反応式

HRID 7821 の反応式
[CH3:1][O:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:12]([CH3:16])([CH2:13]2)[CH2:11][CH2:10][C:9](=[O:17])[CH:8]=3)=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].[Br:23]Br>C(Cl)Cl.CCOC(C)=O>[Br:23][C:8]1[C:9](=[O:17])[CH2:10][CH2:11][C:12]2([CH3:16])[C:7]=1[C:6]1[C:14](=[CH:15][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:13]2

参加物

6

反応物 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 219909037-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 219908604-bromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one収率 46.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (32 mg, 0.14 mmol) and NaHCO3 (60 mg, 0.7 mmol) in CH2Cl2 (0.5 ml) was treated with bromine (0.008 mL, 0.154 mmol), and the resulting mixture was stirred at room temperature for 22 hours. The mixture was diluted with EtOAc (8 ml), washed with dilute aqueous Na2S2O3 (4 mL) and brine (4 ml), dried over MgSO4, filtered, and evaporated under vacuum to a yellow oil (43 mg). This material was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate, developing twice with CH2Cl2, to afford 4-bromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (20 mg) as a gum. The product was contaminated with a trace of 4,6-dibromo-7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one.

後処理

  1. washwashed with dilute aqueous Na2S2O3 (4 mL) and brine (4 ml)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum to a yellow oil (43 mg)
  5. customThis material was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate

出典と根拠

ORDレコード
ord-ca78e012a7fe470cbc127bc7a9674487
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

関連ノート

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