Diethyl Ether → HCID 86607237, compound

HRID 1181853Notes

Reaction equation

P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)CCCCC1.ClC1C(C)=[C:37]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:39][CH:40]=1.[CH2:48](OCC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:48][C:16]1[C:21]([C:39]2[CH:38]=[CH:37][C:41]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:40]=2)=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of potassium phosphate (8.36 g 40 mmol), palladium acetate (0.88 g, 0.4 mmol), 2-(dicyclohexylphosphino)biphenyl (0.54 g, 1.6 mmol) and nphthalene-2-boronic acid (5.09 g, 30 mmol) was added 3-cloro-2-methyl-biphenyl (4.0 g, 20 mmol). The reaction mixture was heated to 80° C. overnight, diluted with diethyl ether, washed with water and dried over MgSO4. Removal of solvent under reduced pressure gave a crude product that was purified by silica gel chromatography eluting with hexanes gave 2-(2-methyl-1,1′-biphenyl-3-yl)naphthalene as a white solid; mp 106-107° C.; MS (EI) m/z 294.17 (M+); 1H NMR (CDCl3): δ 2.15 (s, 3H), 7.20-7.55 (m, 11H), 7.75-7.90 (m, 4H); Anal. Calcd for C23H18: C, 93.84; H, 6.16. Found: C, 93.81; H, 5.95.

Workup

washwashed with water
dry with materialdried over MgSO4
customRemoval of solvent under reduced pressure
customgave a crude product that
customwas purified by silica gel chromatography
washeluting with hexanes

Sources & evidence

ORD record: ord-a7cb82259cbf4fd0b9db6d45605f6a10
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285682B2

Reaction notes

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