Hydrochloric Acid → HCID 59134901, compound

HRID 1993764Notes

Reaction equation

HRID 1993764 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[CH:9][C:8]=1[CH3:18].C[O:20][B:21](OC)[O:22]C.Cl.[OH-].[Na+].P([O-])(O)(O)=O.[Na+]>C1COCC1>[CH3:18][C:8]1[CH:9]=[C:10]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)[CH:11]=[CH:12][C:7]=1[B:21]([OH:22])[OH:20]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 14798Sodium HydroxideHCID 23672064Monosodium phosphateHCID 591349141-(4-Bromo-3-methylphenyl)-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 59134901HCID 59134901, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

n-Butyllithium (7.9 mL of a 2.5 M solution in hexanes, 20 mmol) was added to a solution of compound 2b (4.7 g, 20 mmol) in 100 mL THF at −78° C. The mixture was allowed to warm to −25° C. over 1 hr, then the mixture was cooled to −78° C. Trimethylborate (3.4 mL, 30 mmol) was added and the reaction was allowed to warm to RT. Hydrochloric acid (1N, 100 mL) was then added and the mixture was stirred for 16 hr. The pH of the aqueous layer was adjusted to 3-4 using sodium hydroxide and sodium dihydrogen phosphate solution, then the mixture was extracted with ethyl acetate. The organic layer was concentrated, then the residue was partitioned between ether and 0.5 N sodium hydroxide solution. The aqueous layer was extracted with two additional portions of ether and was then acidified to pH 3-4 using concentrated hydrochloric acid. The mixture was extracted with ethyl acetate, and the combined ethyl acetate extracts were dried over sodium sulfate, filtered, and evaporated to afford 2-methyl-4-(pyrazol-1-yl)phenylboronic acid (compound 2c, 3.5 g) as an amber gum.

Workup

  1. temperaturethe mixture was cooled to −78° C
  2. temperatureto warm to RT
  3. extractionthe mixture was extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customthe residue was partitioned between ether and 0.5 N sodium hydroxide solution
  6. extractionThe aqueous layer was extracted with two additional portions of ether
  7. extractionThe mixture was extracted with ethyl acetate
  8. dry with materialthe combined ethyl acetate extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-42f0a7c988f24e7c9db8900e1c97a856
Source dataset
uspto-grants-2010_01
Patent number
US07652035B2

Reaction notes

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