Tetrahydrofuran → HCID 12927165, compound

HRID 1413550Notes

Reaction equation

HRID 1413550 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([P:9](=[O:12])([O-:11])[O-])=[C:5](C2C=CC=CC=2Br)[C:4]=1[C:20]([F:23])([F:22])[F:21])C.O1[CH2:28][CH2:27][CH2:26][CH2:25]1.[C:29]([Li])(C)([CH3:31])[CH3:30]>CCCCC>[F:23][C:20]([F:21])([F:22])[C:4]1[CH:5]=[C:6]([P:9]2(=[O:12])[C:27]3[CH:28]=[CH:30][CH:29]=[CH:31][C:26]=3[CH2:25][O:11]2)[CH:7]=[CH:8][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 86737158HCID 86737158, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 12927165HCID 12927165, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
-76 °C

Procedure

Under a nitrogen atmosphere a solution of ethyl-2-bromophenyl-3-trifluoromethylphenylphosphonate (2.4 g, 0.00567 mole) in 50 ml. of tetrahydrofuran was cooled to -76° C. by means of a solid carbon dioxide-acetone bath. To the cooled solution was dropwise added a solution of t-butyllithium (0.74 g, 0.0116 mole) in 6.1 ml. of pentane at a rate such that the temperature of the reaction was maintained below -65° C. The reaction mixture was then stirred for one hour at -76° C. after which time the reaction mixture was allowed to increase to 26° C. over a period of 45 minutes. The reaction was quenched with the addition of 1 ml. of acetic acid. The reaction mixture was concentrated under vacuum to yield a yellow residue which was partitioned between methylene chloride and water. The methylene chloride layer was dried over magnesium sulfate and concentrated in vacuo to yield a yellow glass residue. The yellow residue was distilled in a Kugelrohr at 130° C. and 0.2 mm to produce a colorless oil which was crystallized upon trituration in petroleum ether to yield 1-[3-(trifluoromethyl)phenyl]-1,3-dihydro-2,1-benzoxaphosphole-1-oxide (0.85 g, 51% yield) as a white solid having a melting point of 102°-106° C. and the following analysis:

Workup

  1. temperatureto increase to 26° C. over a period of 45 minutes
  2. customThe reaction was quenched with the addition of 1 ml
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customto yield a yellow residue which
  5. customwas partitioned between methylene chloride and water
  6. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto yield a yellow glass residue
  9. distillationThe yellow residue was distilled in a Kugelrohr at 130° C.
  10. custom0.2 mm to produce a colorless oil which
  11. customwas crystallized upon trituration in petroleum ether

Sources & evidence

ORD record
ord-1ea89c4092064ec4aa535a4a001d5645
Source dataset
uspto-grants-1981_02
Patent number
US04250320

Reaction notes

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