Water → HCID 23157353, compound

HRID 507987Notes

Reaction equation

Br[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15])=[CH:4][C:3]=1[CH3:16].[CH:17]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+].O>C(OCC)(=O)C.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.COCCOC>[CH2:14]([O:13][CH2:12][CH2:11][O:10][C:5]1[CH:4]=[C:3]([CH3:16])[C:2]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:17]=[O:18])[CH:24]=2)=[C:7]([CH3:8])[C:6]=1[CH3:9])[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-bromo-5-(2-ethoxyethoxy)-1,3,4-trimethylbenzene (1.16 g, 4.04 mmol), 3-formylphenylboronic acid (0.67 g, 4.44 mmol), tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.20 mmol), cesium carbonate (3.2 g, 9.7 mmol), water (4.8 mL) and 1,2-dimethoxyethane (15 mL) was stirred under a nitrogen atmosphere at 90° C. for 64 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (0.35 g, yield 28%) as a colorless oil.

Workup

washwashed successively with water and saturated brine
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-daf6ee35fac6420bad4768e825d82336
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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