Hydrochloric Acid → 2,3-Difluoro-5-methylphenylboric acid

HRID 2260906Notes

Reaction equation

HRID 2260906 reaction equation
[F:1][C:2]1[C:7]([F:8])=CC=CC=1C.[Li][CH:11](CC)C.[B:15](OC)([O:18]C)[O:16]C.Cl.[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>>[F:1][C:2]1[C:7]([F:8])=[CH:25][C:24]([CH3:11])=[CH:23][C:27]=1[O:26][B:15]([OH:18])[OH:16]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 8470Trimethyl borateHCID 27742282,3-DifluorotolueneHCID 178418400CID 53628100

Product 1

HCID 231188412,3-Difluoro-5-methylphenylboric acid

Procedure

Under a nitrogen atmosphere, 30 g the compound (2) having been dissolved in 240 mL of THF was cooled to −78° C., to which 284 mL of sec-BuLi (1 M/L) was added, followed by stirring at the same temperature for 2 hours. 48.7 g of trimethyl borate having been dissolved in 120 mL of THF was added dropwise thereto at the same temperature, followed by stirring at the same temperature for 1 hour, and the mixture was increased in temperature to room temperature and then stirred over night. Under cooling with an ice bath, 200 mL of 3N hydrochloric acid was added to the mixture. The aqueous layer was extracted with diethyl ether, which was added to the organic layer, and the organic layer was washed with a saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 48.8 g of 2,3-difluoro-5-methylphenylboric acid (3), which was used in the next step without purification.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. stirringby stirring at the same temperature for 1 hour
  4. stirringstirred over night
  5. temperatureUnder cooling with an ice bath
  6. extractionThe aqueous layer was extracted with diethyl ether, which
  7. additionwas added to the organic layer
  8. washthe organic layer was washed with a saturated saline
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-c9212347386743b0a31c65a68a16ad30
Source dataset
uspto-grants-2010_12
Patent number
US07846513B2

Reaction notes

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