Methanol → 253324-72-0

HRID 1071441Notes

Reaction equation

HRID 1071441 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6].[CH:11](Br)(Br)Br.[OH-:15].[K+].[CH3:17][OH:18]>O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([O:6][CH3:11])[C:17]([OH:18])=[O:15])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 5558BromoformHCID 14797Potassium HydroxideHCID 5881603,5-Difluorobenzaldehyde

Product 1

HCID 22392927253324-72-0

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The title compound was prepared according to the general procedure in Reeve, et al, J.A.C.S., 83:2755 (1961). A solution of 3,5-difluorobenzaldehyde (Aldrich) and bromoform (1.2 eq.) In methanol was cooled to −5° C. and treated dropwise with methanolic KOH. The reaction temperature was held below 6 C. during the addition. The mixture was slowly warmed to room temperature and stirred overnight. The suspension was diluted with water and 50% saturated aqueous brine. The mixture was extracted with ether, and the aqueous layer was acidified to a pH around 3.5 and extracted with ether. The latter organic phase was dried over sodium sulfate, filtered and concentrated. The crude acid was purified via flash chromatography eluting with 1:4:95 acetic acid/methanol/methylene chloride to give a white solid. 1H NMR (300 MHz. CDCl3) δ 11.36 (1H, bs), 7.05 (1H, m), 6.81 (2H, tt, J=2.4, 8.8 Hz), 4.77 (1H, s), 3.47 (3H, s)/C9H8F2O3 (MW=202.17); mass spectroscopy—202.

Workup

  1. additionduring the addition
  2. extractionThe mixture was extracted with ether
  3. extractionextracted with ether
  4. dry with materialThe latter organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude acid was purified via flash chromatography
  8. washeluting with 1:4:95 acetic acid/methanol/methylene chloride
  9. customto give a white solid

Sources & evidence

ORD record
ord-288de7d8cb674814a79cdd328cf1ca4b
Source dataset
uspto-grants-2005_06
Patent number
US06906056B2

Reaction notes

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