Ethyl Acetate → t-Butyl [2-(5-cyano-2-iodophenoxy)ethyl]carbamate

HRID 2414401Notes

Reaction equation

HRID 2414401 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[I:21])[C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[C:7]([O:6][C:5]([NH:4][CH2:3][CH2:2][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[I:21])[C:16]#[N:17])=[O:11])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 109446813-Hydroxy-4-iodobenzonitrile

Product 1

HCID 11111864t-Butyl [2-(5-cyano-2-iodophenoxy)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

18.5 g (82.6 mmol) of t-butyl (2-bromoethyl)carbamate was dissolved in 200 ml of DMF. 10.1 g (41.3 mmol) of 3-hydroxy-4-iodobenzonitrile and 5.7 g (41.3 mmol) of potassium carbonate were added to the obtained solution, and they were stirred at 75° C. for 3 hours. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the title compound was obtained.

Sources & evidence

ORD record
ord-044b816ee02f41e68502fdae46d90b00
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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