Acetic Acid → HCID 66737945, compound

HRID 1641616Notes

Reaction equation

HRID 1641616 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](C=[CH:9][CH:10]=1)C(O)=O.[Cl:11][C:12]1[CH:13]=[C:14](I)[CH:15]=[C:16]([Cl:18])[CH:17]=1.[C:20]([OH:23])(=[O:22])[CH3:21].C(CC(C)(C)C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC([O-])=O.[Ag+].C(OCC)(=O)C.ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]([C:4]2[CH:3]=[C:2]([Br:1])[CH:10]=[CH:9][C:21]=2[C:20]([OH:23])=[O:22])[CH:15]=[C:16]([Cl:18])[CH:17]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 109072,2,4-TrimethylpentaneHCID 114563-Bromobenzoic acidHCID 764241,3-Dichloro-5-iodobenzene

Product 1

HCID 66737945HCID 66737945, compound

Reagents, catalysts & solvents 3

HCID 11246Silver acetateCatalystHCID 167845palladium(II) acetateCatalystHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
120 °C

Procedure

Palladium acetate (11.4 mg 0.05 mmol), AgOAc (217 mg 1.3 mmol), 3-bromobenzoic acid (201 mg, 1.0 mmol), 3,5-dichloroiodobenzene (819 mg, 3.0 mmol) and acetic acid (200 μL) were combined and heated at 120° C. for 5.5 h. After purification light tan solid was obtained, 183 mg (53%), mp 182-186° C. (isooctane). Rf-0.38 (1/9 ethyl acetate-dichloromethane). 1H NMR (300 MHz, acetone-d6) δ 7.32 (br s, 2H), 7.36 (d, J-8.4 Hz, 1H), 7.44 (br s, 1H), 7.79 (d, J-8.4 Hz, 1H), 8.05 (br s, 1H). Carboxylate proton signal was not observed. 13C NMR (75 MHz, acetone-d6) δ 122.2, 127.6, 127.7, 133.2, 133.3, 134.6, 135.0, 139.4, 144.5, 166.7. A signal for one aromatic carbon could not be located. FT-IR (neat, cm1) υ 1699, 1299, 857. Anal. calcd for C13H7BrCl2O2 (346.00 g/mol): C, 45.13; H, 2.04. Found: C, 45.17; H, 2.04. The 1H NMR and 13C NMR spectra are shown in FIGS. 27A&B, respectively.

Workup

  1. customAfter purification light tan solid
  2. customwas obtained

Sources & evidence

ORD record
ord-71ccdf8e7a294e3798124385503be803
Source dataset
uspto-grants-2012_02
Patent number
US08114993B2

Reaction notes

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