Hydrochloric Acid → HCID 66693561, compound

HRID 2367980Notes

Reaction equation

HRID 2367980 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([B:13]2[O:17][C:16]([CH3:19])(C)C(C)(C)[O:14]2)=[C:6]([C:9]([F:12])=[CH:10][CH:11]=1)C=O)[CH3:2].[OH-].[Na+].[N+:24](C)([O-:26])=[O:25].Cl>O>[CH2:1]([O:3][C:4]1[C:5]2[B:13]([OH:14])[O:17][CH:16]([CH2:19][N+:24]([O-:26])=[O:25])[C:6]=2[C:9]([F:12])=[CH:10][CH:11]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 86664736HCID 86664736, compound

Product 1

HCID 66693561HCID 66693561, compoundYield 118.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Ethoxy-6-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (1.65 g, 5.61 mmol) was added to a solution of NaOH (225 mg, 5.60 mmol) in H2O (10 mL) and stirred for 10 min at RT. Added nitromethane (1.03 g, 16.83 mmol) dropwise and stirred for 4 h at RT. The reaction mixture was acidified with 4N HCl and extracted with ethyl acetate. Organic layer was washed with water, brine and dried over MgSO4, filtered and concentrated in vacuo. Purification of the residue by flash column chromatography with 10 to 40% EtOAc/hexanes afforded 1.7 g of a mixture of compounds by 1H NMR spectrum. This mixture was used in next step without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.13 (t, J=8.8 Hz, 1H), 6.79 (dd, J=8.8, 2.5 Hz, 1H), 5.95 (d, J=9.0 Hz, 1H), 5.14 (s, 1H), 5.01 (dd, J=13.3, 2.3 Hz, 1H), 4.44 (dd, J=13.3, 9.0 Hz, 1H), 4.10 (q, J=6.8 Hz, 2H), 1.45 (t, J=6.8 Hz, 3H); 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −131.00-−130.97 (m, 1F).

Workup

  1. extractionextracted with ethyl acetate
  2. washOrganic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash column chromatography with 10 to 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-75d4eb21650f4641b08126ded07f71d1
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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