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

HRID 19789노트

반응식

HRID 19789 반응식
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

참가 물질

5

반응물 2

HCID 846761,3-Dibromo-5-chlorobenzeneHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 665209601-Bromo-3-chloro-5-cyclopropylbenzene수율 64%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2b7debaa34934d1abbc3bc7f4dd483ae
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745477B2

반응 노트

불러오는 중…