Ethyl Bromide → 3-Ethoxy-6-fluoro-2-hydroxy-benzaldehyde

HRID 2367979Notes

Reaction equation

HRID 2367979 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH2:12](Br)[CH3:13]>CS(C)=O.O>[CH2:12]([O:11][C:5]1[C:6]([OH:10])=[C:7]([C:2]([F:1])=[CH:3][CH:4]=1)[CH:8]=[O:9])[CH3:13]

Participants

5

Reactant 2

HCID 6332Ethyl BromideHCID 866647326-Fluoro-2,3-dihydroxybenzaldehyde

Product 1

HCID 866647343-Ethoxy-6-fluoro-2-hydroxy-benzaldehydeYield 89.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 6-fluoro-2,3-dihydroxy-benzaldehyde (1.00 g, 6.40 mmol) in dry DMSO (10 mL) was added NaOBut (1.23 g, 12.81 mmol) and ethyl bromide (0.77 g, 7.04 mmol) under N2 and stirred at RT for 18 h. The resultant mixture was diluted with water, acidified to pH ˜6 with 2N.HCl and extracted with EtOAc (4×25 mL). Combined organic layers were washed with water and brine and dried over MgSO4. Filtration and removal of the solvent under reduced pressure provided 1.05 g (5.70 mmol, 89%) of the title compound as yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.24 (s, 1H), 7.04 (dd, J=8.8, 5.3 Hz, 1H), 6.61-6.50 (m, 1H), 4.09 (q, J=7.0 Hz, 3H), 1.46 (t, J=7.0 Hz, 3H); 19F NMR (376 MHz, CHLOROFORM-d) δ ppm −132.19-−132.15 (m, 1F).

Workup

  1. extractionHCl and extracted with EtOAc (4×25 mL)
  2. washCombined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7aefcc4fed0e411585ccf84af0939f53
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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