Hydrochloric Acid → 6-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 532234Notes

Reaction equation

HRID 532234 reaction equation
C(OCOC([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([F:16])=[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:16][C:12]1[C:13]([CH3:15])=[CH:14][C:9]2[C:20]([CH3:22])([CH3:23])[O:21][B:17]([OH:18])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866850962-(2-(2-(Ethoxymethoxy)propan-2-yl)-5-fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 866850956-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-olYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-(2-(ethoxymethoxy)propan-2-yl)-5-fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.35 g, 6.68 mmol) in THF (67 mL) was added 6 N HCl (67 mL). The reaction mixture was stirred at room temperature overnight, and extracted with DCM (200 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (from 10:1 to 3:1) to give 6-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (835 mg, 64%) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.189 (d, J=8.0 Hz, 1H), 6.995 (d, J=6.5 Hz, 1H), 5.950 (s, 1H), 2.266 (s, 3H), 1.472 (s, 6H) ppm.

Workup

  1. extractionextracted with DCM (200 mL×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluted with PE-EA (from 10:1 to 3:1)

Sources & evidence

ORD record
ord-b3695fa135b9475a8b187c112c29f528
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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