Hydrazine hydrate (1:1) → HCID 58239597, compound

HRID 1877708Notes

Reaction equation

HRID 1877708 reaction equation
O.NN.Br[C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:8]=[CH:9][CH:10]=1.[CH2:16]([O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1.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>[CH2:16]([O:23][C:24]1[CH:29]=[C:28]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=2)[CH:27]=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 20638623-(3-bromophenyl)propanoic AcidHCID 27343133-Benzyloxy-phenylboronic acid

Product 1

HCID 58239597HCID 58239597, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

21.5 g (77.2 mmol) of sodium metaborate octahydrate, 0.700 g (977 mmol) of bis(triphenylphosphine)palladium(II) chloride, 0.1 ml (2 mmol) of hydrazine hydrate and 10.0 g (42.3 mmol) of 3-(3-bromophenyl)propionic acid are initially introduced in 10 ml of tetrahydrofuran and 30 ml of water, and a solution of 10.0 g (43.9 mmol) of 3-benzyloxy-benzeneboronic acid in 30 ml of THF is added. The batch is subsequently heated under reflux overnight, added to water and extracted three times with MTB ether. The combined org. phases are filtered through silica gel with heptane/ethyl acetate (1:1), and the crude product is recrystallised from toluene, giving 3-(3′-benzyloxybiphenyl-3-yl)propionic acid as a colourless solid.

Workup

  1. temperatureThe batch is subsequently heated
  2. temperatureunder reflux overnight
  3. extractionextracted three times with MTB ether
  4. filtrationphases are filtered through silica gel with heptane/ethyl acetate (1:1)
  5. customthe crude product is recrystallised from toluene

Sources & evidence

ORD record
ord-3d432cd8574c4394894736dfdffdbc7c
Source dataset
uspto-grants-2012_11
Patent number
US08313669B2

Reaction notes

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