Hydrochloric Acid → 3-Ethoxy-4-fluoro-2-hydroxybenzaldehyde

HRID 2368014Notes

Reaction equation

HRID 2368014 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[C:8]([F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].I[CH2:13][CH3:14].Cl>CS(C)=O>[CH2:13]([O:10][C:9]1[C:2]([OH:1])=[C:3]([CH:6]=[CH:7][C:8]=1[F:11])[CH:4]=[O:5])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 451191034-Fluoro-2,3-dihydroxybenzaldehyde

Product 1

HCID 866647473-Ethoxy-4-fluoro-2-hydroxybenzaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,3-dihydroxy-4-fluorobenzaldehyde (3.0 g, 19.23 mmol) in DMSO (100 mL), NaOBu-t (3.692 g, 38.46 mmol) was added in portions at room temperature and stirred for 15 min. Then iodoethane was added dropwise at room temperature and stirred for 18 h. The reaction mixture was poured onto crushed ice (200 mL) and acidified with 2.5 M HCl to pH 3.0. The product was extracted with ethyl acetate (2×100 mL), concentrated and the product was chromatographed on a column of silica gel (Hex:EtOAc=95:5) to give the title compound as a crystalline solid (2.3 g, 65%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 11.36 (s, 1H), 9.83 (s, 1H), 7.39-7.19 (m, 1H), 6.77 (t, J=9.2 Hz, 1H), 4.22 (q, J=7.0 Hz, 2H), 1.40 (t, J=7.0 Hz, 3H); MS (ESI) m/z=183 (M+1, positive).

Workup

  1. stirringstirred for 18 h
  2. additionThe reaction mixture was poured
  3. extractionThe product was extracted with ethyl acetate (2×100 mL)
  4. concentrationconcentrated
  5. customthe product was chromatographed on a column of silica gel (Hex:EtOAc=95:5)

Sources & evidence

ORD record
ord-eaca5ed3c232493f9073b3806df0f946
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

Loading…