Triethylamine → 2-Chloro-4-(trifluoromethyl)-benzeneacetic acid methyl ester
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=[O:14].[CH2:16](N(CC)CC)C.[NH4+].[Cl-]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:16][O:14][C:13](=[O:15])[CH2:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=1[Cl:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
2-Chloro-4-(trifluoromethyl)-benzeneacetic acid (3 g) [CAS Reg. No. 601513-26-2] was dissolved in DCM (30 mL) and methyl chloroformiate (1.18 g, 0.97 mL) followed by triethylamine (1.4 g, 1.93 mL) were added drop by drop. To the mixture was added DMAP (0.154 g) and the yellow mixture was allowed to stir for 1 hour at 0° C. A clear solution was obtained. The mixture was diluted with DCM (30 mL) and was poured into sat. NH4Cl solution. The layers were separated and the aqueous phase was further extracted with 2 portions of DCM. The organic layers were washed with brine, dried over Na2SO4 and evaporated to give the title compound (3.0 g) that was used without further purification. NMR, (CDCl3): 7.6-7.4 (m, 3H); 3.84 (s, 2H); 3.74 (s, 3H).
Workup
- additionwere added drop by drop
- customA clear solution was obtained
- customThe layers were separated
- extractionthe aqueous phase was further extracted with 2 portions of DCM
- washThe organic layers were washed with brine
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-3f49432e722541b0a187816e3371d5be
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883786B2
Reaction notes
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