Sodium Carbonate → Tert-butyl 2-acetoxy-2-(4'-(trifluoromethoxy)biphenyl-3-yl)acetate

HRID 1751772Notes

Reaction equation

[C:1]([O:4][CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>C(#N)C.O.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>[C:1]([O:4][CH:5]([C:13]1[CH:14]=[C:15]([C:32]2[CH:31]=[CH:30][C:29]([O:28][C:27]([F:26])([F:38])[F:39])=[CH:34][CH:33]=2)[CH:16]=[CH:17][CH:18]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of compound 3 (811 mg, 2.46 mmol), Na2CO3 (650 mg, 6.13 mmol), Pd(PPh3)4 (207 mg, 0.18 mmol) and 4-trifluoromethoxy phenyl boronic acid (870 mg, 4.22 mmol) in acetonitrile (7.0 mL) and water (0.7 mL) was heated to 130° C. in the microwave for 30 minutes. The mixture was filtered through Celite® diatomaceous earth and washed with EtOAc. The filtrate was concentrated in vacuo and the resulting residue was purified by flash chromatography (80 g silica cartridge, 0-10% EtOAc/hexanes) to provide compound 4.

Workup

filtrationThe mixture was filtered through Celite® diatomaceous earth
washwashed with EtOAc
concentrationThe filtrate was concentrated in vacuo
customthe resulting residue was purified by flash chromatography (80 g silica cartridge, 0-10% EtOAc/hexanes)

Sources & evidence

ORD record: ord-9785a8cc8e414b6389ab089e14987704
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09161924B2

Reaction notes

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