Methanol → 5-Hydroxy-[1,1'-biphenyl]-2-carbaldehyde

HRID 445832Notes

Reaction equation

HRID 445832 reaction equation
Br[C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+].CO>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.C(OCC)(=O)C.C1(C)C=CC=CC=1>[OH:10][C:8]1[CH:9]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 887MethanolHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 110848662-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 573034645-Hydroxy-[1,1'-biphenyl]-2-carbaldehyde

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-4-hydroxybenzaldehyde (350 mg, 1.74 mmol), phenyl boronic acid (233.5 mg, 1.92 mmol), Pd(PPh3)4 (60 mg, 0.052 mmol), saturated sodium bicarbonate (6.0 mL), methanol (15 mL), and toluene (6.0 mL) was heated in a pressure tube at 120° C. overnight. Ethyl acetate and water were added and the layers separated. The aqueous phase was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (30%) to afford 5-hydroxy-[1,1′-biphenyl]-2-carbaldehyde (651).

Workup

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (30%)

Sources & evidence

ORD record
ord-95808328835545a5bc47789b00b2f2db
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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