Hydrazine hydrate (1:1) → HCID 58239601, compound

HRID 1877711Notes

Reaction equation

HRID 1877711 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.O.NN.[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=2)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1

Participants

7

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 728512-(4-Bromophenyl)ethanolHCID 4374257(3,5-Dimethoxyphenyl)boronic acid

Product 1

HCID 58239601HCID 58239601, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

20 g (99 mmol) of 2-(4-bromophenyl)ethanol, 20 g (72 mmol) of sodium metaborate octahydrate and 2.0 g (2.8 mmol) of bis(triphenylphosphine)palladium(II) chloride are initially introduced in 30 ml of THF and 120 ml of water, and, after addition of 0.03 ml of hydrazine hydrate, a solution of 15.5 g (85 mmol) of 3,5-dimethoxybenzeneboronic acid in 60 ml of THF is added dropwise. The batch is heated under reflux overnight and subsequently extracted four times with dichloromethane. The combined org. phases are washed with water and dried over sodium sulfate. The solvent is removed in vacuo, and the crude product is chromatographed on silica gel with heptane/ethyl acetate (2:1), giving 2-(3′,5′-dimethoxybiphenyl-4-yl)ethanol as a colourless solid.

Workup

  1. temperatureThe batch is heated
  2. temperatureunder reflux overnight
  3. extractionsubsequently extracted four times with dichloromethane
  4. washphases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed in vacuo
  7. customthe crude product is chromatographed on silica gel with heptane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-084413a640194ab19e55a23ec8f449f0
Source dataset
uspto-grants-2012_11
Patent number
US08313669B2

Reaction notes

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