Tetrabutylammonium Fluoride → Diethyl 5-(cyanomethyl)benzene-1,3-dioate

HRID 2261884Notes

Reaction equation

HRID 2261884 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH2:12]Br)[CH:9]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1)=[O:5])[CH3:2].[F-].[CH2:20]([N+:24](CCCC)(CCCC)CCCC)CCC>CC#N>[C:20]([CH2:12][C:10]1[CH:9]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=1)#[N:24]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10935954Diethyl 5-(Bromomethyl)isophthalate

Product 1

HCID 59709094Diethyl 5-(cyanomethyl)benzene-1,3-dioate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of diethyl-5-(bromomethyl)benzene-1,3-dioate (1.9 g, 6.0 mmol) in 69 mL MeCN was added trimethylsilyl cyamide (1.2 mL, 9.0 mmol) and tetrabutylammonium fluoride (1M in THF, 9.0 mL, 9.0 mmol). The reaction was stirred for 0.5 h and concentrated. Flash chromatography (silica gel, 0-30% EtOAc/hexanes) gave diethyl 5-(cyanomethyl)benzene-1,3-dioate. 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 8.20 (app t, J=0.7 Hz, 2H), 4.43 (q, J=7.1 Hz, 4H), 3.86 (s, 2H), 1.43 (t, J=7.1 Hz, 6H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-64814dff184f4619a9946bad92e2a74d
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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