1,2-Dimethoxyethane → HCID 20099919, compound

HRID 511984Notes

Reaction equation

HRID 511984 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)=[O:19].[OH-].[Ba+2].[OH-].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.O>[CH3:16][O:17][C:18]([C:20]1[CH:25]=[C:24]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 6093286Barium hydroxide

Product 1

HCID 20099919HCID 20099919, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.176 g, 0.67 mmol), 3-methoxycarbonylphenylboronic acid (0.18 g, 1 mmol), barium hydroxide (0.25 g, 1.47 mmol), Pd(PPh3)4 (0.077 g, 0.067 mmol), DME (5 mL) and H2O (3 mL) was microwaved with vigorous stirring using a CEM-discover system (ram time: 2 min, hold time: 5 min, temperature: 120° C., pressure: 200 psi, power: 250 W). The crude reaction mixture filtered through a plug of celite and concentrated in vacuo. The residue obtained was purified by flash column chromatography (25% diethyl ether-hexane) to give the title compound (29) (0.118 g, 60% yield) as a viscous liquid.

Workup

  1. customwas microwaved
  2. customa CEM-discover system (ram time: 2 min, hold time: 5 min, temperature: 120° C., pressure: 200 psi, power: 250 W)
  3. customThe crude reaction mixture
  4. filtrationfiltered through a plug of celite and
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas purified by flash column chromatography (25% diethyl ether-hexane)

Sources & evidence

ORD record
ord-2d3b5417475f47ce89ce76555d8a0443
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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