Bromine → 2,6-dibromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

HRID 1684866

反応式

HRID 1684866 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1.[Br:14]Br>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH:10]([Br:14])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:13]=1

参加物

4

反応物 2

HCID 24408BromineHCID 102433122-bromo-6,7,8,9-tetrahydro-5H-benzo(7)annulen-5-one

生成物 1

HCID 672659642,6-dibromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one収率 37.3%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

Example 3, 2-Bromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (1.5 g, 5.9 mmol) was dissolved Et2O (25 mL), cooled to 0° C. and bromine (0.35 mL, 6.6 mmol) was added dropwise. The solution was stirred at 24° C. until TLC indicated reaction complete (2-18 h; scale dependent). The solvent was removed by rotory evaporation and the crude product applied to a 25 (M) Biotage® silica gel column. Gradient elution from 50-100% B (A=Hexanes; B=10% EtOAc/hex) over 500 mL and gave 2,6-dibromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one 700 mg, and 1.5 g of a second fraction containing dibromide (1:1). RT=2.2 minutes (condition 1).

後処理

  1. customreaction complete (2-18 h; scale dependent)
  2. customThe solvent was removed by rotory evaporation
  3. washGradient elution from 50-100% B (A=Hexanes

出典と根拠

ORDレコード
ord-c43970141c9d45e3885f0b0716f641d1
出典データセット
uspto-grants-2012_04
特許番号
US08147818B2

関連ノート

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