1,2-Dimethoxyethane → 3'-(Benzyloxy)[1,1'-biphenyl]-3-carbonitrile

HRID 512009Notes

Reaction equation

HRID 512009 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.[C:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)#[N:17].[OH-].[Ba+2].[OH-].COCCOC>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.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:22]2[CH:23]=[C:18]([CH:19]=[CH:20][CH:21]=2)[C:16]#[N:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 27343253-Cyanophenylboronic acidHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 6093286Barium hydroxide

Product 1

HCID 200999373'-(Benzyloxy)[1,1'-biphenyl]-3-carbonitrileYield 60%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.2 g, 0.76 mmol), 3-cyanophenylboronic acid (0.223 g, 1.52 mmol), barium hydroxide (0.285 g, 1.67 mmol), Pd(PPh3)4 (0.088 g, 0.076 mmol), DME (5 mL) and H2O (3 mL) was heated (80° C.) for 6 hours with vigorous stirring under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a plug of celite. The filtrate was diluted with brine; the organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue obtained was purified by flash column chromatography (20% diethyl ether-hexane) to give 75 (0.130 g, 60% yield) as a viscous liquid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a plug of celite
  3. additionThe filtrate was diluted with brine
  4. customthe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. customwas purified by flash column chromatography (20% diethyl ether-hexane)

Sources & evidence

ORD record
ord-4095be00623b4fb4a45dac4721c6654a
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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