Water → HCID 59558703, compound

HRID 1175172Notes

Reaction equation

HRID 1175172 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].Br[CH2:12][CH2:13][O:14][CH2:15]CBr.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(OC(=O)C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:12][CH2:13][O:14][CH3:15])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 27570145-Bromo-2-hydroxybenzonitrile

Product 1

HCID 59558703HCID 59558703, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-2-hydroxy-benzonitrile (5.4 g, 27.0 mmol), 2-bromoethylether (2.76 ml, 29.7 mmol) and K2CO3 (4.5 g, 32.4 mmol) are mixed in 50 ml DMF. The reaction mixture is stirred at 50 C overnight. Addition of water and extraction into ethylacetate yields the title compound which is further purified by tituration with ether/hexanes. 1H-NMR (400 MHz; DMSO-d6): 7.99 (d, 1H), 7.82 (dd, 1H), 7.23 (d, 1H), 4.27 (t, 2H), 3.69 (t, 2H), 3.33 (s, 3H). LC-MS (m/z, ES+): 273 (M+NH4+), retention time: 2.77 mins (LC-MS method 3)

Sources & evidence

ORD record
ord-bddcd21414fd40cd8e8678834e71b3d6
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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