Potassium Phosphate, Tribasic → 1-Chloro-3,5-dicyclopropylbenzene

HRID 2363194Notes

Reaction equation

HRID 2363194 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4](Br)[CH:3]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:37]2[CH2:42][CH2:41]CCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[C:6]([CH:10]2[CH2:12][CH2:11]2)[CH:5]=[C:4]([CH:41]2[CH2:42][CH2:37]2)[CH:3]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 846761,3-Dibromo-5-chlorobenzeneHCID 2760897Cyclopropylboronic acid

Product 1

HCID 671118831-Chloro-3,5-dicyclopropylbenzeneYield 477.5%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

1-Chloro-3,5-dibromobenzene (2.70 g, 10.0 mmol) and cyclopropylboronic acid (1.72 g, 20 mmol) were reacted using K3PO4 (14.9 g, 70 mmol), tricyclohexylphosphine (56 mg, 2.0 mmol), Pd(OAc)2 (288 mg, 1.0 mmol) as described above to give 1-chloro-3,5-dicyclopropyl-benzene (1.84 g, 96%) after purification by flash chromatography on silica gel (% EtOAc in hexane=2%˜10%).

Sources & evidence

ORD record
ord-4bbce9305f8c4579ae598837a7ca25ea
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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