Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 23039573, compound

HRID 437604Notes

Reaction equation

HRID 437604 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:7][CH:8]=1.[N:13]1([CH2:19][CH2:20][C:21]([CH:23]2[CH2:25][CH2:24]2)=[O:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl-:26].[NH4+]>CCOCC>[ClH:26].[CH:23]1([C:21]([C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:4]=2)([OH:22])[CH2:20][CH2:19][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 21488082HCID 21488082, compound

Product 1

HCID 23039573HCID 23039573, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The Grignard reagent prepared from 14.5 g. (0.6 mole) of magnesium and 136 g. (0.6 mole) of m-bromobenzotrifluoride in 800 ml. of dry ether was cooled to -30° C. and treated with 53.5 g. (0.296 mole) of crude cyclopropyl 2-piperidinylethyl ketone in 200 ml. of ether at a rate that the temperature was maintained below -20° C. After addition, the mixture was stirred and allowed to warm to room temperature over a one-hour period. The reaction mixture was treated with 32 g. of ammonium chloride in 170 ml. of water and the ether layer was separated. The remainder of the reaction mixture was filtered and the resulting solid precipitate was extracted with five 200 ml. portions of ether. The combined ether extracts were dried over magnesium sulfate and concentrated to an oil. The oil was distilled under reduced pressure and the distillate was converted to the hydrochloride salt. Recrystallization from acetone-ethanol mixture gave 3.6 g. (17%) of pure product which melted at 193°-194° C. after drying.

Workup

  1. additiontreated with 53.5 g
  2. additionAfter addition
  3. additionThe reaction mixture was treated with 32 g
  4. customof water and the ether layer was separated
  5. filtrationThe remainder of the reaction mixture was filtered
  6. extractionthe resulting solid precipitate was extracted with five 200 ml
  7. dry with materialThe combined ether extracts were dried over magnesium sulfate
  8. concentrationconcentrated to an oil
  9. distillationThe oil was distilled under reduced pressure
  10. customRecrystallization from acetone-ethanol mixture
  11. customgave 3.6 g
  12. dry with material(17%) of pure product which melted at 193°-194° C. after drying

Sources & evidence

ORD record
ord-7a1e4af42489419bb1bea7f3aba9bc8f
Source dataset
uspto-grants-1977_06
Patent number
US04031245

Reaction notes

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