Hydrochloric Acid → HCID 86685087, compound

HRID 1750844Notes

Reaction equation

HRID 1750844 reaction equation
C(OCOC([C:9]1[C:14]([F:15])=[C:13]([CH3:16])[CH:12]=[CH:11][C:10]=1[B:17]1[O:21][C:20]([CH3:23])([CH3:22])C(C)(C)[O:18]1)(C)C)C.Cl>C1COCC1>[F:15][C:14]1[C:9]2[C:20]([CH3:22])([CH3:23])[O:21][B:17]([OH:18])[C:10]=2[CH:11]=[CH:12][C:13]=1[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86685088HCID 86685088, compound

Product 1

HCID 86685087HCID 86685087, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude compound 2-(2-(2-(ethoxymethoxy)propan-2-yl)-3-fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.17 g, 14.7 mmol) in THF (147 mL) was added 6 N HCl (147 mL). The reaction mixture was stirred at room temperature overnight, and the resulting mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried over with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (10:1) to give 4-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (1.52 g, 53.8% yield over 2 steps) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.339 (d, J=7.5 Hz, 1H), 7.200 (t, J=6.5 Hz, 1H), 5.652 (s, 1H), 2.330 (s, 3H), 1.642 (s, 6H) ppm.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluted with PE-EA (10:1)

Sources & evidence

ORD record
ord-ca0b4bb8379f46a9a273ac8fc03a0417
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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