4-Bromobenzyl bromide → HCID 66578489, compound

HRID 1529035Notes

Reaction equation

HRID 1529035 reaction equation
[CH:1]1([C:4]#[N:5])[CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1>C1COCC1>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:1]2([C:4]#[N:5])[CH2:3][CH2:2]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 685274-Bromobenzyl bromideHCID 79637CyclopropanecarbonitrileHCID 2724682Lithium diisopropylamide

Product 1

HCID 66578489HCID 66578489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cyclopropanecarbonitrile (2.5 g, 37.3 mmol) was added to a solution of lithium diisopropylamide (41 mmol) in THF (20 mL) at −78° C. and the reaction stirred for 1 hour. 1-Bromo-4-bromomethyl-benzene (10.25 g, 41 mmol) in THF (50 mL) was slowly added and the reaction was allowed to warm to room temperature over 30 minutes. The reaction was submitted to standard aqueous workup to afford the title compound, which was used in the next step without further purification.

Sources & evidence

ORD record
ord-86deb884a28b47db87d343e8d7ab6cfe
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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