Diisopropylethylamine → 2'-Nitro-4'-(trifluoromethyl)-[1,1'-biphenyl]-3-acetic acid ethyl ester

HRID 1696454Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].CCN(C(C)C)C(C)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:4]1[CH:3]=[C:2]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][C:16]=2[N+:25]([O-:27])=[O:26])[CH:7]=[CH:6][CH:5]=1)[CH3:13]

Participants

Conditions

Temperature: 130 °C

Procedure

Ethyl 2-(3-iodophenyl)acetate (0.500 g, 1.72 mmol), 4-bromo-3-nitrobenzotrifluoride (1.86 g, 6.89 mmol commercially available), tetrabutylammonium chloride (0.527 g, 1.90 mmol), i-Pr2NEt (0.33 mL, 1.90 mmol) and Pd(OAc)2 (0.039 g, 0.17 mmol) were combined neat in a sealed vial and heated at 130° C. for 65 h. The cooled reaction mixture was applied directly to silica gel and eluted with 25% EtOAc/hexanes to provide 2′-nitro-4′-(trifluoromethyl)-[1,1′-biphenyl]-3-acetic acid ethyl ester (0.107 g, 17% yield). MS (ESI) m/z: 354.0 (M+H+).

Workup

customThe cooled reaction mixture
washeluted with 25% EtOAc/hexanes

Sources & evidence

ORD record: ord-dbc0c5fd6e3944be89c75cdbbf37f216
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163756B2

Reaction notes

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