Methanol → HCID 23157554, compound

HRID 507934Notes

Reaction equation

HRID 507934 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[CH2:11]([O:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=1Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CO>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.C1(C)C=CC=CC=1>[CH2:11]([O:18][C:19]1[C:20]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 27343604-Hydroxyphenylboronic acidHCID 23111814Methyl 4-(benzyloxy)-3-bromobenzoate

Product 1

HCID 23157554HCID 23157554, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

(4-Hydroxyphenyl)boronic acid (5.0 g, 36.3 mmol), methyl 4-benzyloxy-3-bromobenzoate (7.0 g, 21.8 mmol) and cesium carbonate (18.0 g, 55.2 mmol) were added to a mixed solution of methanol (50 mL) and toluene (100 mL), the air was substituted with argon gas, and tetrakis(triphenylphosphine)palladium(0) (0.45 g, 0.39 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 70° C. for 2 days. After cooling the reaction mixture, the insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:5-2:1), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (5.0 g, yield 69%) as colorless prism crystals.

Workup

  1. additionwas added
  2. temperatureAfter cooling the reaction mixture
  3. filtrationthe insoluble material was filtered off through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-3247b0d7836949f792ca562ffbec39a8
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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