2-Bromobenzyl alcohol → HCID 1393999, compound

HRID 2423057Notes

Reaction equation

HRID 2423057 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[CH:10]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)=[O:11].C(=O)(O)[O-].[Na+]>COCCO.O.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>[OH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[C:15]1[CH:16]=[CH:17][C:12]([CH:10]=[O:11])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 728502-Bromobenzyl alcoholHCID 516892Sodium BicarbonateHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 1393999HCID 1393999, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 22504935Water 2-methoxyethanolSolvent

Procedure

i)—To a solution of 2-bromo-benzylalcohol (5 g, 26.7 mmol) in 2-methoxyethanol/water (30 ml, 1/1) were added 4-formylphenylboronic acid (6 g, 40.0 mmol) and sodium bicarbonate (4.4 g, 52.4 mmol) under a nitrogen atmosphere. After (Ph3P)4Pd (1.54 g, 1.34 mmol) was added, the reaction mixture was heated under reflux for 17 h. After cooling, the mixture was filtered over dicalite and the residue was washed with water and ethyl acetate. The product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate concentrated under reduced pressure. Column chromatography afforded 2′-hydroxymethyl-biphenyl-4-carbaldehyde (3.95 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 17 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered over dicalite
  5. washthe residue was washed with water and ethyl acetate
  6. extractionThe product was extracted into ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2547622b8885440bb6b2596b3709ca0d
Source dataset
uspto-grants-2011_06
Patent number
US07960560B2

Reaction notes

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