1,3-Dibromo-5-chlorobenzene → 1-Bromo-3-chloro-5-cyclopropylbenzene

HRID 19789ノート

反応式

HRID 19789 の反応式
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.[CH:10]1([Mg]Br)[CH2:12][CH2:11]1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:9][C:4]1[CH:3]=[C:2]([CH:10]2[CH2:12][CH2:11]2)[CH:7]=[C:6]([Cl:8])[CH:5]=1

参加物

5

反応物 2

HCID 846761,3-Dibromo-5-chlorobenzeneHCID 178418630HCID 178418630、化合物

生成物 1

HCID 665209601-Bromo-3-chloro-5-cyclopropylbenzene収率 64%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a solution of 1,3-dibromo-5-chlorobenzene (500 mg, 1.85 mmol) in THF (1 ml) was added cyclopropylmagnesium bromide (3698 μl, 0.5M solution in THF, 1.85 mmol) in a sealed tube and the reaction mixture was degassed with argon for 5 min before tetrakis(triphenylphosphine)palladium (0) (107 mg, 0.09 mmol) was added. The resulting solution was heated to 70° C. overnight, cooled to RT and then quenched with sat. NH4Cl solution and extracted with pentane. The organic phases were combined, washed with water and brine, dried over MgSO4 and filtered through a short pad of silica gel to give the desired product (272 mg, 64%) which did not require further purification. 1H NMR (CDCl3, 300 MHz): 7.28 (aptt, J=2.0 Hz, 1H), 7.08 (aptt, J=1.5 Hz, 1H), 6.97 (aptt, J=1.5 Hz, 1H), 1.83 (m, 1H), 1.04-0.97 (m, 2H), 0.72-0.67 (m, 2H).

後処理

  1. additionwas added
  2. temperaturecooled to RT
  3. customquenched with sat. NH4Cl solution
  4. extractionextracted with pentane
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered through a short pad of silica gel

出典と根拠

ORDレコード
ord-2b7debaa34934d1abbc3bc7f4dd483ae
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

反応ノート

読み込み中…