1,2-Dimethoxyethane → 4-Methoxybiphenyl

HRID 1372156Notes

Reaction equation

HRID 1372156 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].I[C:19]1[CH:20]=[CH:21][C:22](C)=[C:23](O)[CH:24]=1.COCCOC>CCOC(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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 114362355-Iodo-2-methylphenol

Product 1

HCID 119434-MethoxybiphenylYield 50.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methoxyphenylboronic acid (4.55 g, 21.38 mmol), Na2CO3 (32.1 ml 2 N aqueous, 64.2 mmol), Pd(PPh3)4 (1.24 g, 1.07 mmol), 5-iodo-2-methylphenol (Hodgson, Moore J. Chem. Soc. 1926, 2038) (5.0 g, 21.38 mmol), and ethylene glycol dimethyl ether (225 ml) was heated to reflux overnight. The reaction was cooled, diluted with EtOAc and the layers separated. The organic layer was dried over anhydrous Na2SO4, passed through a silica plug and concentrated. Chromatography (30% EtOAc/hexanes) afforded 1.64 g (36%) product as a white solid and 2 g 4-methoxy biphenyl as an undesired by-product: mp 146–147° C.; 1H NMR (300 MHz, DMSO-d6): δ 2.13 (3H, s), 3.78 (3H, s), 6.94 (1H, dd, J=8.1 Hz, 2.7 Hz), 7.00 (3H, m), 7.09 (1H, d, J=8.1 Hz), 7.48 (1H, d, J=9.5 Hz), 9.36 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction was cooled
  4. customthe layers separated
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c7cf71043f9a42a1964a09b094491faa
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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