Potassium Carbonate → tert-Butyl 4'-methyl[1,1'-biphenyl]-2-carboxylate

HRID 1851876Notes

Reaction equation

Br[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].B(O)(O)[C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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.O>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([C:2]2[C:3]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 350 mL high-pressure vial was added tert-butyl 2-bromobenzoate (5.142 g, 20.0 mmol), p-tolylboronic acid (4.08 g, 30.0 mmol), Pd(PPh3)4 (3.47 g, 3.0 mmol), potassium carbonate (8.29 g, 60.0 mmol) and dioxane with water (4:1, 200 mL). The mixture was degassed for 5 min and sealed. The mixture was heated at 100° C. for 40 min wherein analytical HPLC analysis indicated the completion of the reaction. The mixture was filtered through Celite and MeOH was used to wash the Celite pad. The solvent was removed and the crude was purified by flash chromatography (AcOEt/Hexane 0→30%) to obtain the title compound.

Workup

customThe mixture was degassed for 5 min
customsealed
customthe completion of the reaction
filtrationThe mixture was filtered through Celite and MeOH
washto wash the Celite pad
customThe solvent was removed
customthe crude was purified by flash chromatography (AcOEt/Hexane 0→30%)

Sources & evidence

ORD record: ord-1080ada4e13244dfb40303ebddc6cbf8
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957093B2

Reaction notes

Loading…