Ethyl bromoacetate → [4-(Trifluoromethyl)-1H-imidazol-1-yl]acetic acid ethyl ester

2.0 g (14.7 mmol) 4-(trifluoromethyl)-1H-imidazole are initially introduced into 5.5 ml (4.7 g, 14.7 mmol) 21% strength sodium ethylate solution in ethanol and 1.8 ml (2.7 g, 16.2 mmol) ethyl bromoacetate are added. The reaction mixture is stirred at RT for 16 h. For working up, the solid which has precipitated out is filtered off, the residue on the filter is washed with ethanol and the filtrate is concentrated in vacuo. Diisopropyl ether is added to the residue, the mixture is filtered again, the filtrate is concentrated again on a rotary evaporator and the residue is dried in vacuo. The product is obtained as a 9:1 mixture of the two regioisomers and is further reacted as such.

1. additionare added
2. customthe solid which has precipitated out
3. filtrationis filtered off
4. washthe residue on the filter is washed with ethanol
5. concentrationthe filtrate is concentrated in vacuo
6. additionDiisopropyl ether is added to the residue
7. filtrationthe mixture is filtered again
8. concentrationthe filtrate is concentrated again on a rotary evaporator
9. customthe residue is dried in vacuo
10. customThe product is obtained as a 9:1 mixture of the two regioisomers
11. customis further reacted as such

ORD record

ord-6ff10ab8616d4f208a376441ebf097e7

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987261B2