[1.1.1]Propellane → HCID 68380148, compound

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.[CH2:11]1[C:13]23[CH2:15][C:12]12[CH2:14]3>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]12[CH2:15][CH:13]([CH2:14]1)[CH2:11]2

Participants

Reactant 2

HCID 142022[1.1.1]Propellane

HCID 178489560HCID 178489560, compound

Product 1

HCID 68380148HCID 68380148, compound

Procedure

Reaction of 2-methoxyphenylmagnesium bromide with [1.1.1]propellane (see A. B. Shtarev et al., J. Am. Chem. Soc. 2001, 123, 3484-3492) afforded 1-(2-methoxyphenyl)bicyclo[1.1.1]pentane, which was treated with boron tribromide to provide the requisite phenol.

Sources & evidence

ORD record: ord-5d2b47cb286e4479b1cb68c0d551cf8f
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067934B2

Reaction notes

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