Hydrochloric Acid → HCID 86685507, compound

HRID 1037063Notes

Reaction equation

HRID 1037063 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]C)=[CH:6][C:5]([B:10]2[O:14]C(C)(C)C(C)(C)O2)=[C:4]([C:19]([O:22]COCC)([CH3:21])[CH3:20])[CH:3]=1.Cl.O>C1COCC1>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[B:10]([OH:14])[O:22][C:19]([CH3:20])([CH3:21])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86685508HCID 86685508, compound

Product 1

HCID 86685507HCID 86685507, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-chloro-2-(2-(ethoxymethoxy)propan 2-yl)-5-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.77 g, 4.8 mmol) in THF (24 mL) was added 6N HCl (24 mL). The reaction mixture was stirred at rt overnight. Water was added and the mixture was extracted with EA. The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography eluted with PE-EA (20:1) to give 5-chloro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (540 mg; yield 53.6% over 2 steps) as a light yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 9.13 (s, 1H), 7.62 (s, 1H), 7.54 (s, 1H), 2.36 (s, 3H), 1.46 (s, 6H) ppm; MS: m/z=210.9 (M+1, ESI+).

Workup

  1. extractionthe mixture was extracted with EA
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with PE-EA (20:1)

Sources & evidence

ORD record
ord-61b48074bcd249529b7d3079a05275a8
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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