4-Bromotoluene → HCID 434533, compound

HRID 1870861Notes

Reaction equation

HRID 1870861 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][N:15]1[CH:20]2[CH2:21][CH2:22][CH:16]1[CH2:17][C:18](=[O:23])[CH2:19]2>O1CCCC1>[CH3:14][N:15]1[CH:20]2[CH2:21][CH2:22][CH:16]1[CH2:17][C:18]([C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)([OH:23])[CH2:19]2

Participants

5

Reactant 3

HCID 78054-BromotolueneHCID 79038Npc164516HCID 178418339Butyllithium

Product 1

HCID 434533HCID 434533, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 4-bromotoluene (13.9 g, 81.4 mmol), n-butyllithium in hexanes (31.2 mL, 2.5 M; 78 mmol) and 8-methyl-8-azabicyclo[3.2.1]-octan-3-one (5 g, 35.9 mmol) in anhydrous tetrahydrofuran (40 mL). Yield 3.5 g (42%) as a white solid, m.p. 247-249° C.

Sources & evidence

ORD record
ord-baf512550d8b47efaad7b28a26b10257
Source dataset
uspto-grants-2000_08
Patent number
US06100275

Reaction notes

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