Hydrazine hydrate (1:1) → HCID 66671212, compound

HRID 1877714Notes

Reaction equation

HRID 1877714 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]=[CH:12][C:13]1[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[CH2:24]([O:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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>[CH2:24]([O:31][C:32]1[CH:37]=[C:36]([C:17]2[CH:16]=[CH:15][C:14]([OH:20])=[C:13]([CH:12]=[CH:11][CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:18]=2)[CH:35]=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 27343133-Benzyloxy-phenylboronic acidHCID 66671213HCID 66671213, compound

Product 1

HCID 66671212HCID 66671212, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

10.3 g (31 mmol) of 2-(4-benzyloxybut-1-enyl)-4-bromophenol, 5.5 g (20 mmol) of sodium metaborate octahydrate and 0.6 g (0.84 mmol) of bis(triphenylphosphine)palladium(II) chloride are initially introduced in 20 ml of THF and 60 ml of water, and, after addition of 0.03 ml of hydrazine hydrate, a solution of 6.0 g (26 mmol) of 3-benzyloxybenzeneboronic acid in 40 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 recrystallised once each from toluene and ethanol, giving 3′-benzyloxy-3-(4-benzyloxybut-1-enyl)biphenyl-4-ol 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 recrystallised once each from toluene and ethanol

Sources & evidence

ORD record
ord-64a1ca72e88e479e97633d2c196acbdc
Source dataset
uspto-grants-2012_11
Patent number
US08313669B2

Reaction notes

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