Potassium Phosphate, Tribasic → Methyl 2'-formyl-3'-methoxy-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

HRID 2167145Notes

Reaction equation

Cl[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([O:14][CH3:15])[C:3]=1[CH:4]=[O:5].[CH3:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC(O)=O.CC(O)=O.[Pd]>[CH:4]([C:3]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:2]=1[C:23]1[CH:24]=[CH:25][C:20]([C:18]([O:17][CH3:16])=[O:19])=[CH:21][CH:22]=1)=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

2-Chloro-6-methoxy-4-(trifluoromethyl)benzaldehyde (224 mg, 0.94 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (219 mg, 1.22 mmol), S-PHOS (115 mg, 0.28 mmol), Pd(Oac)2 (32 mg, 0.14 mmol) and K3PO4 (597 mg, 2.81 mmol) were dissolved in wet PhMe (8 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

extractionextracted with EtOAc
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated
custompurified via column chromatography

Sources & evidence

ORD record: ord-021c7943dc3246688865febbcf8e9216
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045389B2

Reaction notes

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