Diiodomethane → 5'-Bromo-2',3'-dihydrospiro[cyclopropane-1,1'-indene]

HRID 855312노트

반응식

HRID 855312 반응식
[CH2:1]([Zn]CC)C.FC(F)(F)C(O)=O.C(I)I.[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[C:22](=[CH2:26])[CH2:21][CH2:20]2>>[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[C:22]1([CH2:1][CH2:26]1)[CH2:21][CH2:20]2

참가 물질

5

반응물 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 588409305-bromo-1-methylene-2,3-dihydro-1H-indeneHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 695138995'-Bromo-2',3'-dihydrospiro[cyclopropane-1,1'-indene]수율 95%

실험 절차

The title compound was synthesized in analogy to example S87 using diethyl zinc (3.25 ml, 1M solution in hexane, 3.25 mmol), trifluoroacetic acid (251 μl, 3.25 mmol), CH2I2 (262 μl, 3.25 mmol) and 5-bromo-1-methyleneindan (340 mg, 1.63 mmol). The isolated residue was purified by flash column chromatography (100% pentane) to give 5′-bromo-2′,3′dihydro-spiro[cyclopropane1,1′-[1H]indene](345 mg, 95%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.40-7.29 (m, 3H), 3.02 (apt t, J=7.5 Hz, 2H), 2.11 (apt t, J=7.5 Hz, 2H), 0.96-0.84 (m, 4H).

후처리

  1. customThe isolated residue was purified by flash column chromatography (100% pentane)

출처 및 근거

ORD 기록
ord-9ddf1306b93441acb3699c69273971fa
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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