Methanol → HCID 54371494, compound

HRID 963217Notes

Reaction equation

HRID 963217 reaction equation
CO.[OH-].[K+].[Br:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[OH:13].[S:14]([O:24][CH2:25][C:26]#[C:27][CH2:28][CH2:29]OS(C1C=CC(C)=CC=1)(=O)=O)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15]>C(O)(=O)C>[S:14]([O:24][CH2:25][CH2:26][C:27]#[C:28][CH2:29][O:13][C:7]1[CH:8]=[CH:9][C:10]([F:12])=[CH:11][C:6]=1[Br:5])([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:15])=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 6054722-Bromo-4-fluorophenolHCID 54106401HCID 54106401, compound

Product 1

HCID 54371494HCID 54371494, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To MeOH (140 mL) solution containing KOH (4.73 g, 84.3 mmol) at 22° C. was added 2-bromo-4-fluorophenol (16.09 g, 84.2 mmol) and 2-pentyne-1,5-diol ditosylate (11.47 g, 28.1 mmol). After stirring 20 h acetic acid (3.5 mL) was added and the reaction stirred 1 h. The reaction was concentrated in vacuo and the residue extracted with CH2Cl2 (75 mL) and saturated K2CO3 (75 mL). The organic phase was separated and washed with saturated K2CO3. The aqueous phase was washed with CH2Cl2 (2×30 mL). The combined CH2 Cl2 layers were dried with dried with MgSO4, filtered, concentrated in vacuo. Silica gel chromatography (9:1 Hexane:EtOAc) yielded the title compound as a viscous oil (8.39 g, 70%).

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated in vacuo
  3. extractionthe residue extracted with CH2Cl2 (75 mL) and saturated K2CO3 (75 mL)
  4. customThe organic phase was separated
  5. washwashed with saturated K2CO3
  6. washThe aqueous phase was washed with CH2Cl2 (2×30 mL)
  7. dry with materialThe combined CH2 Cl2 layers were dried
  8. dry with materialwith dried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b248aaf49e84f72bc559fa7c96883e1
Source dataset
uspto-grants-1998_06
Patent number
US05763444

Reaction notes

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