Chlorobenzene → HCID 57543425, compound

HRID 1641618Notes

Reaction equation

HRID 1641618 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-:7])=[O:6])[CH:3]=1.Cl[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:21](P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)CCC.C([O-])([O-])=O.[Cs+].[Cs+].C[Si](C=[N+]=[N-])(C)C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[C:15]1([C:8]2[CH:9]=[CH:10][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:3][C:4]=2[C:5]([O:7][CH3:21])=[O:6])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

9

Reactant 5

HCID 7964ChlorobenzeneHCID 10796Cesium carbonateHCID 167693TrimethylsilyldiazomethaneHCID 69512791,3-Benzenedicarboxylic acid, monomethyl esterHCID 11371790Bis(adamantan-1-yl)(butyl)phosphane

Product 1

HCID 57543425HCID 57543425, compoundYield 747.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Palladium acetate (5.6 mg, 0.025 mmol), mono-methyl isophthalate (90 mg, 0.5 mmol) and chlorobenzene (283 mg, 2.5 mmol), butyldi-1-adamantylphosphine (19.2 mg, 0.05 mmol), Cs2CO3 (358 mg, 1.1 mmol), molecular sieves 3 Å (155 mg) and anhydrous DMF (2.5 mL). After the reaction and workup the residue was dissolved in methanol (10 mL) and cooled to 0° C. (Trimethylsilyl)diazomethane in hexanes (5.0 ml of a 2.0M solution, 1 mmol) was added dropwise, the cooling bath was removed and the mixture stirred for 5 h. The solvent was removed under reduced pressure. Purification by preparative HPLC afforded 101 mg (75%) of a colorless oil. Analytical data are consistent with that of previously reported data.4 1H NMR (300 MHz, CDCl3) δ 3.67 (s, 3H), 3.95 (s, 3H), 7.30-7.47 (m, 6H), 8.15-8.18 (m, 1H), 8.5 (br s, 1H). The 1H NMR spectrum is shown in FIG. 38.

Workup

  1. customAfter the reaction and workup the residue
  2. additionwas added dropwise
  3. customthe cooling bath was removed
  4. customThe solvent was removed under reduced pressure
  5. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-9fd51971e9e14f968f2ff03056f5cc5a
Source dataset
uspto-grants-2012_02
Patent number
US08114993B2

Reaction notes

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