1,2-Dimethoxyethane → HCID 21071796, compound

HRID 1372166Notes

Reaction equation

HRID 1372166 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+].Br[C:19]1[C:27]2[O:26][CH:25]=[CH:24][C:23]=2[CH:22]=[C:21]([CH3:28])[CH:20]=1.COCCOC>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.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:19]2[C:27]3[O:26][CH:25]=[CH:24][C:23]=3[CH:22]=[C:21]([CH3:28])[CH:20]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 210718017-Bromo-5-methyl-1-benzofuran

Product 1

HCID 21071796HCID 21071796, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-methoxyphenylboronic acid (4.76 g, 31.3 mmol), Na2CO3 (32.6 2 N aqueous, 65.2 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol), 7-bromo-5-methylbenzofuran (5.5 g, 26.1 mmol), and ethylene glycol dimethyl ether (275 ml) was heated to reflux for 12 h. The reaction was cooled, ether (500 ml) was added and the layers separated. The aqueous was further extracted with ether and the organic layers were dried over anhydrous Na2SO4, passed through a silica plug and concentrated to 7.16 g brown oil. Further purification by column chromatography (10% EtOAc/hexanes) afforded 5.62 g (91%) product as a clear oil: 1H NMR (300 MHz, DMSO-d6): δ 3.44 (3H, s), 3.82 (3H, s), 6.94 (1H, d, J=2.2 Hz), 7.108 (2H, d, J=8.8 Hz), 7.30 (1H, s), 7.38 (1H, s), 7.81 (2H, d, J=8.8 Hz), 8.00 (1H, d, J=2.2 Hz).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. temperatureThe reaction was cooled
  4. customthe layers separated
  5. extractionThe aqueous was further extracted with ether
  6. dry with materialthe organic layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated to 7.16 g brown oil
  8. customFurther purification by column chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cc029056401141c68e021c347462c23b
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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