Hydrochloric Acid → 5-Bromo[1,1'-biphenyl]-3-ol

HRID 420409Notes

Reaction equation

HRID 420409 reaction equation
Br[C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].Cl>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.C1(C)C=CC=CC=1>[Br:8][C:6]1[CH:5]=[C:4]([OH:9])[CH:3]=[C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 122803,5-DibromophenolHCID 66827Phenylboronic Acid

Product 1

HCID 156614915-Bromo[1,1'-biphenyl]-3-ol

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Toluene (400 mL) and water (20 mL) were added to a mixture of 3-,5-dibromophenol (5.088 g, 19.85 mmol), phenylboronic acid (2.42 g, 19.85 mmol) and potassium carbonate (5.48 g, 39.7 mmol) in a round bottom flask. This was followed by addition of 1.149 g of tetrakis(triphenylphosphine)palladium(0) under a atmosphere of nitrogen. This mixture was stirred at heated overnight at 90° C. At this time, HCl (2 N aq) was added to the reaction mixture until pH=˜2 and the subsequent two phases were separated; the aqueous phase was extracted and washed three time with ethyl acetate. The combined organic phases were dried with MgSO4, filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo to provide an orange oil. Analysis of the oil by LC/MS indicated a mixture of desired product, starting material and the bis-phenyl coupling product The mixture was carried on to the next aryl boronic acid coupling step 2.

Workup

  1. customthe subsequent two phases were separated
  2. extractionthe aqueous phase was extracted
  3. washwashed three time with ethyl acetate
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. filtrationfiltered
  6. washwashed with ethyl acetate
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto provide an orange oil

Sources & evidence

ORD record
ord-85f57fa805c34683bfaf27b709c47403
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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