Hydrochloric Acid → HCID 20042590, compound

HRID 1761936Notes

Reaction equation

HRID 1761936 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[N:17]([CH:21]([CH3:26])[C:22](OC)=[O:23])[N:18]=[N:19][CH:20]=1.Cl>O1CCCC1.O>[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:17]2[N:18]=[N:19][CH:20]=[N:16]2)[CH3:26])=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 5462224MagnesiumHCID 20042589Methyl 2-(2H-tetrazol-2-yl)propanoate

Product 1

HCID 20042590HCID 20042590, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-trifluoromethoxybromobenzene (45.79 g) in dry tetrahydrofuran (200 cm3) was added carefully to a stirred mixture of magnesium turnings (4.56 g), iodine (1 crystal) and dry tetrahydrofuran (70 cm3). The reaction commenced after about 20 cm3 of the solution had been added, and the reaction was maintained at the reflux temperature whilst the remainder of the solution was added, and thereafter for a further 1 hour. The mixture was cooled to the ambient temperature and a solution of methyl 2-(1,2,3,4-2H-tetrazol-2-yl)propionate (13.95 g), in dry tetrahydrofuran (60 ml) added dropwise, after which the mixture was heated at the reflux temperature for 30 minutes. The mixture was cooled and poured into water (500 cm3) and acidified with 2N hydrochloric acid (250 cm3). The aqueous mixture was extracted with diethylether (3×400 cm3), the ethereal extracts combined, dried over anhydrous magnesium sulphate, and concentrated by removal of the solvent by evaporation under reduced pressure. The residual oil (30.5 g) was subjected to purification by chromatography using a silica gel column eluted with a mixture of hexane (4 parts by volume) and ethylacetate (1 part by volume), and by hplc to yield 1,1-bis(4-trifluoromethoxyphenyl)-2-(1,2,3,4-2H-tetrazol-2-yl)propan-1-ol as a colourless oil (10 g) which crystallized on standing (mp. 55°-58° C.).

Workup

  1. additionhad been added
  2. temperaturethe reaction was maintained at the reflux temperature whilst the remainder of the solution
  3. additionwas added
  4. temperatureafter which the mixture was heated at the reflux temperature for 30 minutes
  5. temperatureThe mixture was cooled
  6. extractionThe aqueous mixture was extracted with diethylether (3×400 cm3)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. concentrationconcentrated by removal of the solvent by evaporation under reduced pressure
  9. customThe residual oil (30.5 g) was subjected to purification by chromatography
  10. washeluted with a mixture of hexane (4 parts by volume) and ethylacetate (1 part by volume)

Sources & evidence

ORD record
ord-1b026828e4f64a6c90c62e35a5e4b001
Source dataset
uspto-grants-1989_05
Patent number
US04829074

Reaction notes

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