Hydrochloric Acid → HCID 433777, compound

HRID 1761938Notes

Reaction equation

HRID 1761938 reaction equation
BrC1C=C[C:5]([O:8]C(F)(F)F)=[CH:4]C=1.[Mg].II.[N:16]1[N:17]([CH:21]([CH3:34])[C:22](C2C=CC(C(F)(F)F)=CC=2)=[O:23])[N:18]=[N:19][CH:20]=1.Cl>O1CCCC1.O>[CH2:5]([O:8][C:22](=[O:23])[CH:21]([N:17]1[N:18]=[N:19][CH:20]=[N:16]1)[CH3:34])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 5462224MagnesiumHCID 20042602HCID 20042602, compound

Product 1

HCID 433777HCID 433777, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The Grignard reagent from 4-bromotrifluoromethoxybenzene (2.41 g) was prepared in a similar manner to that described in Example 3 from magnesium turnings (0.24) in dry tetrahydrofuran (14 ml) with iodine (1 crystal) as an activator. To the Grignard solution was added dropwise over 10 minutes 2-(2H-tetrazol-2-yl)p-trifluoromethylpropiophenone from Example 16 (2.7 g in dry tetrahydrofuran (10 ml), then the reaction stirred for 1 hour. The reaction was worked up as for previous examples, by pouring into water, acidifying with aqueous hydrochloric acid and extracting the product into diethyl ether, which was dried over anhydrous sodium sulphate and evaporated. The residual oil (4.3 g) was purified by h.p.l.c. on silica gel eluting with 5:1 hexane/ethyl acetate to give a colourless oil 2.3 g.

Workup

  1. extractionextracting the product into diethyl ether, which
  2. dry with materialwas dried over anhydrous sodium sulphate
  3. customevaporated
  4. customThe residual oil (4.3 g) was purified by h.p.l.c

Sources & evidence

ORD record
ord-b10ea6c60d1440499395f9fad1dac228
Source dataset
uspto-grants-1989_05
Patent number
US04829074

Reaction notes

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