2-Bromopropane → 2-(3,4-Dimethoxyphenyl)-3-methylbutanenitrile

HRID 2119099Notes

Reaction equation

[OH-].[Na+].[CH2:3]([C:14]#[N:15])[C:4]1[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[C:6]([O:7][CH3:8])[CH:5]=1.[CH:16](Br)([CH3:18])[CH3:17]>CC[N+](CC1C=CC=CC=1)(CC)CC.[Cl-]>[CH:16]([CH:3]([C:14]#[N:15])[C:4]1[CH:13]=[CH:12][C:9]([O:10][CH3:11])=[C:6]([O:7][CH3:8])[CH:5]=1)([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 50 °C

Procedure

27.83 g of 50% NaOH solution, 5.84 g (145.95 mmol) of NaOH pellets and veratryl cyanide (8.9 g, 50.24 mmol) were placed in a 100 ml round-bottom flask. 2.05 g (9.02 mmol) of TEBAC was added and the mixture was stirred until homogenous while heating to 50° C. with a heating mantle. Isopropyl bromide (5.5 ml, 58.58 mmol) was added dropwise over 0.5 h at 50° C.±5° to the above mixture which was stirred at 50° C.±5° for 24 hours. The reaction mixture was partitioned between water and toluene and transferred to a separatory funnel. The aqueous layer was drawn off and extracted with ether. The toluene and ether fractions were combined and washed twice with water and dried over Na2SO4. The mixture was filtered and solvent removed by rotary evaporation. The combined fractions, following evaporation and recrystallization from 70 percent methanol/water yielded 6.32 g of the title compound (57% yield).

Workup

stirringwas stirred at 50° C.±5° for 24 hours
customThe reaction mixture was partitioned between water and toluene
customtransferred to a separatory funnel
extractionextracted with ether
washwashed twice with water
dry with materialdried over Na2SO4
filtrationThe mixture was filtered
customsolvent removed by rotary evaporation
customevaporation and recrystallization from 70 percent methanol/water

Sources & evidence

ORD record: ord-519f1f5abe3544d8ba3a2ead31fb91f4
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04681970

Reaction notes

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