1-Bromo-4-fluorobenzene → HCID 131723327, compound

HRID 2188367Notes

Reaction equation

HRID 2188367 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[CH3:10][N:11]([CH:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=[O:20])[CH3:12].[Cl-:27].[NH4+]>CCOCC>[ClH:27].[CH3:12][N:11]([CH:13]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1([C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1)[OH:20])[CH3:10]

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 131723327HCID 131723327, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

0.50 g (20.7 mmole) of magnesium turnings was stirred in 10 ml of ether of analysis purity. 2.28 ml (20.7 mmole) of 4-bromofluorobenzene dissolved in 20 ml of ether were added dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was stirred for a further hour at RT. 4.0 g (17.3 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 were dissolved in 10 ml of ether, added dropwise to the Grignard reagent while cooling in an ice bath, and stirred for 15 hours at RT. The reaction solution was worked up by adding 30 ml of saturated ammonium chloride solution while cooling in an ice bath, and was extracted three times at RT with in each case 80 ml of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 5.50 9 of crude base (97.2% of theory) were obtained. 3.61 g of 2-(dimethylaminophenylmethyl)-1-(4-fluorophenyl)cyclohexanol, hydrochloride (57.4% of theory) were obtained from the crude base according to the procedure described in Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The hydrochloride decomposes on heating above 150° C.

Workup

  1. additionwere added dropwise so that the reaction mixture
  2. additionAfter completion of the addition the reaction mixture
  3. temperaturewhile cooling in an ice bath
  4. stirringstirred for 15 hours at RT
  5. temperaturewhile cooling in an ice bath
  6. extractionwas extracted three times at RT with in each case 80 ml of ethyl acetate
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)
  10. custom5.50 9 of crude base (97.2% of theory) were obtained

Sources & evidence

ORD record
ord-35eed225c67646a9b68198e8ae6bc60c
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

Loading…