Iodine → HCID 13504096, compound

HRID 1762479Notes

Reaction equation

HRID 1762479 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.[Mg].II.[N:16]1([CH:21]([CH3:26])[C:22](OC)=[O:23])[CH:20]=[N:19][CH:18]=[N:17]1>O1CCCC1>[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:22]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:11])[F:12])=[CH:9][CH:8]=2)([OH:23])[CH:21]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH3:26])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 807IodineHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 2768671HCID 2768671, compoundHCID 5462224Magnesium

Product 1

HCID 13504096HCID 13504096, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
40 °C

Procedure

A solution of 4-trifluoromethoxybromobenzene (9.3 g) in dry tetrahydrofuran (40 cm3)was added dropwise to a stirred mixture of magnesium turnings (0.93 g), dry tetrahydrofuran (15 cm3) and a crystal of iodine under a nitrogen atmosphere and at the ambient temperature. The reaction was observed to have commenced after 4 cm3 of the solution had been added. After the addition was complete the mixture was stirred for a further 2 hours. A solution of methyl 2-(1,2,4-1H-triazol-1-yl)propionate (3.0 g) in dry tetrahydrofuran (5.0 cm3) was added dropwise to the mixture and after stirring for a further two hours at the ambient temperature the mixture was warmed to 40° C. for 3 hours. The mixture was then quenched with water, acidified with dilute hydrochloric acid and extracted with diethyl ether. The ethereal extract was washed with water (three times) and dried over anhydrous magnesium sulphate. The residual oil remaining after removal of the solvent by evaporation under reduced pressure was subjected to purification by hplc using a silica gel column eluted with a mixture of dichloromethane (3 parts by volume) and ethyl acetate (2 parts by volume) to give 1,1-bis(4-trifluoromethoxyphenyl)-2-(1,2,4-1H-triazol-1-yl)propanol (1.0 l g) as a solid residue.

Workup

  1. customat the ambient temperature
  2. additionhad been added
  3. additionAfter the addition
  4. stirringafter stirring for a further two hours at the ambient temperature the mixture
  5. customThe mixture was then quenched with water
  6. extractionextracted with diethyl ether
  7. extractionThe ethereal extract
  8. washwas washed with water (three times)
  9. dry with materialdried over anhydrous magnesium sulphate
  10. customafter removal of the solvent
  11. customby evaporation under reduced pressure
  12. customwas subjected to purification by hplc
  13. washeluted with a mixture of dichloromethane (3 parts by volume) and ethyl acetate (2 parts by volume)

Sources & evidence

ORD record
ord-4a62c9ae6a0c4308bcf3c75523320dec
Source dataset
uspto-grants-1989_05
Patent number
US04833159

Reaction notes

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