Tetrahydrofuran → HCID 57592471, compound

HRID 1784401Notes

Reaction equation

HRID 1784401 reaction equation
[CH3:1][O:2][C:3]1[C:4]([S:15](F)(=[O:17])=[O:16])=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8][C:7]=2[CH:14]=1.O1CCCC1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O.C(OCC)C>[F:24][C:25]1[CH:30]=[CH:29][C:28]([S:15]([C:4]2[C:3]([O:2][CH3:1])=[CH:14][C:7]3[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=3[CH:5]=2)(=[O:17])=[O:16])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 2724148Sodium potassium tartrate tetrahydrateHCID 57592494HCID 57592494, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 57592471HCID 57592471, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

The sulfonyl fluoride D4 from Description 4 (25 g) was dissolved it dry tetrahydrofuran (250 mL) and 4-fluorophenylmagnesium bromide in tetrahydrofuran (2.5 equivalents) added over 15 min with ice bath cooling, an exotherm only apparent during the first part of the addition. Stirred overnight without cooling then added over 10 min to a solution of sodium potassium tartrate tetrahydrate (250 g) in water (450 mL) with stirring. Diethyl ether was added (400 mL) and the organic layer separated, dried, evaporated, and crystallised from diethyl ether to give crystalline fluorophenyl sulfone D5 17 g (51%).

Workup

  1. additionadded over 15 min with ice bath
  2. temperaturecooling
  3. additionan exotherm only apparent during the first part of the addition
  4. temperaturewithout cooling
  5. stirringwith stirring
  6. customthe organic layer separated
  7. customdried
  8. customevaporated
  9. customcrystallised from diethyl ether

Sources & evidence

ORD record
ord-2b6ab01f798244e8b1487d9e6a44336f
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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