Borane;tetrahydrofuran → 1-[1-(4-Bromophenyl)cyclopropyl]methanamine

HRID 1853915Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.B.C1COCC1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:11][NH2:12])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 2723981Borane;tetrahydrofuran

HCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

Product 1

HCID 289378461-[1-(4-Bromophenyl)cyclopropyl]methanamineYield 94%

Procedure

Following the procedure outlined for Example 666, 1-(4-bromophenyl)cyclopropane carbonitrile (2.0 g, 9.0 mmol) was reacted with BH3.THF (1.0 M in THF, 50 mL, 50 mmol) to afford the desired product (1.9 g, 94%) as a yellow oil: ESI MS m/z 226 [C10H12BrN+H]+.

Sources & evidence

ORD record: ord-dd0fd6b6bd85428abd2f8032c04c1d81
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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