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1,3-Dichloro-5-(trifluoromethyl)benzene → 1-Chloro-3-cyclopropyl-5-(trifluoromethyl)benzene

HRID 2363186
Notes
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Reaction equation

HRID 2363186 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:13]1(B(O)O)[CH2:15][CH2:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=[C:2]([CH:13]2[CH2:15][CH2:14]2)[CH:7]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 353611,3-Dichloro-5-(trifluoromethyl)benzeneHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 671109241-Chloro-3-cyclopropyl-5-(trifluoromethyl)benzeneYield 87.1%

Reagents, catalysts & solvents 1

HCID 167845
palladium(II) acetate
Catalyst

Procedure

3,5-Dichlorobenzotrifluoride (1.10 g, 5.1 mmol) and cyclopropylboronic acid (440 mg, 5.1 mmol) were reacted using K3PO4 (3.8 g, 17.9 mmol), tricyclohexylphosphine (145 mg, 0.51 mmol), Pd(OAc)2 (60 mg, 0.27 mmol) as described in example 100 to give 1-chloro-3-cyclopropyl-5-trifluoromethyl-benzene (980 mg, 87%) after purification by flash chromatography on silica gel.

Sources & evidence

ORD record
ord-f35752fe12fa40f99a6f2d2e92dfff17
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691855B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes