Benzyl mercaptan → HCID 57523125, compound

HRID 79013Notes

Reaction equation

HRID 79013 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[C:23](F)[C:22]=1[F:30])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[C:23]([S:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:22]=1[F:30])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 23665647Potassium tert-butoxideHCID 57523124HCID 57523124, compound

Product 1

HCID 57523125HCID 57523125, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium tert-butoxide (2.0 g, 17.9 mmol) in anhydrous THF (80 mL) was added benzyl mercaptan (2.1 mL, 17.9 mmol). The reaction mixture was stirred at room temperature for 5 minutes before being cooled to −30° C. A solution of 2,3-difluoro-4-formyl-benzoic acid tert-butyl ester (4.34 g, 17.9 mmol) in anhydrous THF (20 mL) was added dropwise over 15 minutes and the resultant mixture was stirred at −30° C. for 30 minutes before being quenched by addition of water and extracted with ethyl acetate. The organic layer was separated, washed with water followed by brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a yellow oil (6.2 g, 100%). 1H NMR (CDCl3, 400 MHz) 10.20 (1 H, d, J=0.6 Hz), 7.84 (1 H, ddd, J=8.0, 6.8, 0.7 Hz), 7.59 (1 H, dd, J=8.0, 0.9 Hz), 7.19 (3 H, m), 7.05 (2 H, m), 4.07 (2 H, s), 1.63 (9 H, s).

Workup

  1. temperaturebefore being cooled to −30° C
  2. custombefore being quenched by addition of water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-6d36d1b4f9914ec4a7056c583b6151a3
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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