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

HRID 855312ノート

反応式

HRID 855312 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-9ddf1306b93441acb3699c69273971fa
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

反応ノート

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