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

HRID 855312Notes

Reaction equation

[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

Participants

Reactant 4

HCID 6346Diiodomethane

HCID 6422Trifluoroacetic acid

HCID 588409305-bromo-1-methylene-2,3-dihydro-1H-indene

HCID 178418750HCID 178418750, compound

Product 1

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

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-9ddf1306b93441acb3699c69273971fa
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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