Hydrochloric Acid → 4'Propyl-2-fluoro-4-biphenylboronic acid

HRID 1033695Notes

Reaction equation

HRID 1033695 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)=[C:4]([F:17])[CH:3]=1.[Mg].[B:19](OC)([O:22]C)[O:20]C.Cl>O1CCCC1>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:19]([OH:22])[OH:20])=[CH:3][C:4]=2[F:17])=[CH:9][CH:10]=1)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 5462224MagnesiumHCID 227175064-Bromo-2-fluoro-4'-propyl-1,1'-biphenyl

Product 1

HCID 157450984'Propyl-2-fluoro-4-biphenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
75 °C

Procedure

The product from step (ii) (10 g; 0.034 mol) in tetrahydrofuran (35 ml) was added dropwise to a suspension of magnesium turnings (0.88 g) in tetrahydrofuran (5 ml). The mixture was warmed to 75° C. when the Grignard reaction started. Further of the bromo compound was slowly added and the external heat source removed, a gentle reflux being maintained. After complete addition, the mixture was heated for 30 mins under reflux and then cooled to 15° C. A dry nitrogen atmosphere was introduced and trimethyl borate (3.77 g; 0.0363 mol) was slowly added and the mixture stirred at 15°-20° C. for 16 hrs. A 20% soln of hydrochloric acid (50 ml) was slowly added, the organic layer was separated, and the aqueous layer extracted with ether (2×50 ml). The combined organic layers were washed with brine and dried over sodium sulphate. Upon evaporation of the solvents a yellow solid was obtained. Yield 8.7 g; 100%.

Workup

  1. customthe Grignard reaction
  2. customthe external heat source removed
  3. temperaturea gentle reflux
  4. temperaturebeing maintained
  5. additionAfter complete addition
  6. temperaturethe mixture was heated for 30 mins
  7. temperatureunder reflux
  8. temperaturecooled to 15° C
  9. additionA dry nitrogen atmosphere was introduced
  10. customthe organic layer was separated
  11. extractionthe aqueous layer extracted with ether (2×50 ml)
  12. washThe combined organic layers were washed with brine
  13. dry with materialdried over sodium sulphate
  14. customUpon evaporation of the solvents a yellow solid
  15. customwas obtained

Sources & evidence

ORD record
ord-afe33dcb24184ed8a7121681b79d33d7
Source dataset
uspto-grants-1994_05
Patent number
US05312563

Reaction notes

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