Ethyl bromoacetate → HCID 847306, compound

HRID 1660918Notes

Reaction equation

HRID 1660918 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:11]([O:13][C:14](=[O:17])[CH2:15]Br)[CH3:12].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:11]([O:13][C:14](=[O:17])[CH2:15][O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[C:7]#[N:8])[CH3:12]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27774205-Chloro-2-hydroxybenzonitrile

Product 1

HCID 847306HCID 847306, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-chloro-2-hydroxy-benzonitrile (10 g, 65.0 mmol) in acetone (100 mL) was added ethylbromoacetate (11 g, 71.4 mmol) followed by K2CO3 (19.7 g, 143 mmol). After heating at reflux for 10 h, the mixture was filtered and the filtrate was concentrated to afford the desired product (15.3 g), which was used in the next step without further purification. 1H NMR (CDCl3): 7.57 (d, J=2.5 Hz, 1H), 7.48 (dd, J=9.0, 2.5 Hz, 1H), 6.81 (d, J=9.0 Hz 1H), 4.78 (s, 2H), 4.28 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 10 h
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9914d308739242b7a73d359e969a6e51
Source dataset
uspto-grants-2011_10
Patent number
US08030321B2

Reaction notes

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