Hydrochloric Acid → HCID 59689163, compound

HRID 2425272Notes

Reaction equation

HRID 2425272 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.[BH4-].[Na+].Cl>C(OCC)C.O1CCCC1.CO>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([CH:19]([NH2:20])[C:18]2[CH:21]=[CH:22][C:15]([C:14]([F:13])([F:23])[F:24])=[CH:16][CH:17]=2)=[CH:4][CH:5]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 4311764Sodium borohydrideHCID 5462224Magnesium

Product 1

HCID 59689163HCID 59689163, compoundYield 2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5 mmol magnesium-turnings in 10 ml diethyl ether was treated with 5 mmol 4-bromobenzotrifluoride to form the corresponding Grignard-reagent. This reagent was slowly added to a cooled solution of 5 mmol 4-(trifluoromethyl)benzonitrile in 10 ml of tetrahydrofuran at −70° C. After 1 hour at −70° C., the reaction mixture was stirred additional 2 hours at room temperature and then refluxed overnight. The resulting mixture was cooled again to 0° C. and diluted with 10 ml of methanol and 10 mmol sodium borohydride were added. After stirring for 2 hours at room temperature, the mixture was poured into 100 ml of 0.5 M aqueous hydrochloric acid and extracted with diethyl ether. The aqueous phase was adjusted to pH=10 by addition of diluted aqueous sodium hydroxide and extracted 3 times with dichloromethane. Chromatography (SiO2; dichloromethane/methanol) yielded the title compound as a slightly brown foam.

Workup

  1. customto form the corresponding Grignard-reagent
  2. temperaturerefluxed overnight
  3. temperatureThe resulting mixture was cooled again to 0° C.
  4. additionwere added
  5. stirringAfter stirring for 2 hours at room temperature
  6. extractionextracted with diethyl ether
  7. additionThe aqueous phase was adjusted to pH=10 by addition of diluted aqueous sodium hydroxide
  8. extractionextracted 3 times with dichloromethane

Sources & evidence

ORD record
ord-43755f424924437597b4e4a7b5756afb
Source dataset
uspto-grants-2011_06
Patent number
US07964645B2

Reaction notes

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