Sodium Carbonate → 5-(Methylsulfonyl)biphenyl-2-carboxylic acid methyl ester

HRID 1499240Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:15][S:12]([C:10]1[CH:11]=[C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=1)(=[O:14])=[O:13]

Participants

Conditions

Temperature: 160 °C

Procedure

To a mixture of methyl 2-chloro-4-(methylsulfonyl)benzoate (2.2 g, 8.9 mmol), PhB(OH)2 (1.31 g, 10.8 mmol), DME (12 mL), and 2M Na2CO3 (6 mL) was added Pd(PPh3)4 (515 mg). The mixture was heated for 20 min at 160° C. in a microwave reactor, and then extracted with EtOAc, dried over sodium sulfate and concentrated in vacuo. Purification on normal phase silica gel (hexane/EtOAc) provided methyl 5-(methylsulfonyl)-[1,1′-biphenyl]-2-carboxylate as a white solid.

Workup

extractionextracted with EtOAc
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customPurification on normal phase silica gel (hexane/EtOAc)

Sources & evidence

ORD record: ord-2f9b8a66f54d4b45b25e418afcc4572b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199994B2

Reaction notes

Loading…