Citric Acid → HCID 89704694, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[CH2:13]C(O)=O.CC[N:19](CC)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[Si](C)(C)[O-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[CH2:13][NH2:19]Participants
7
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 2,4-dichloro-6-trifluoromethylphenylacetic acid (0.36 mmol) in 3 mL toluene were added Et3N (0.44 mmol) and DPPA (0.36 mmol). The reaction mixture was heated to 110° C. for 3 h, cooled to 0° C. and a solution of potassium trimethylsilanolate (0.73 mmol, 1M in THF) was added. After stirring at RT for 30 min, an aqueous solution of 10% citric acid was added and the mixture was extracted twice with Et2O. The aqueous phase was basified with 1M NaOH solution and extracted 3 times with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as white solid.
Workup
- temperaturecooled to 0° C.
- extractionthe mixture was extracted twice with Et2O
- extractionextracted 3 times with DCM
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cd512eb600d84e62b94ed65a81c22abc
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409917B2
Reaction notes
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