Potassium Phosphate, Tribasic → 2'-Phenyl-2,4,6-trimethylbiphenyl

HRID 510566

Reaction equation

[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1B(O)O.Br[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH3:25].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P1C2C(C3C(OC)=CC=CC=3OC)=CC=CC=2OC1)(C)(C)C.C1(C)C=CC=CC=1>[C:10]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of biphenyl-2-ylboronic acid (0.15 g, 0.75 mmol, 1.5 equiv) and 2-bromo-1,3,5-trimethylbenzene (100 mg, 0.5 mmol, 1.0 equiv), tris(dibenzylideneacetone)dipalladium (0.46 mg, 0.0005 m mol, 0.1 mol %), 3-tert-butyl-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole (0.66 mg, 0.04 mmol, 0.4 mol %), and potassium phosphate (0.318 g, 1.5 mmol, 3 equiv) was charged dagassed toluene (4 mL). The mixture was stirred at 70° C. under nitrogen for 3 h, then quenched with water (4 mL). The organic phase was separated, washed with brine, dried over sodium sulfate, concentrated, and purified by column chromatography to provide pure desired product as oil (129 mg, 0.48 mmol, 95%). ESI-MS: m/z 273 [M+H]+.

Workup

customquenched with water (4 mL)
customThe organic phase was separated
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
custompurified by column chromatography

Sources & evidence

ORD record: ord-c80c1c0d96ee43289e1f52343c5ec4c7
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096626B2

Linked notes

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