p-Bromochlorobenzene → HCID 131723326, compound

HRID 2188366Notes

Reaction equation

HRID 2188366 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Cl: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-].[NH4+]>CCOCC>[ClH:9].[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([C:15]2([OH:20])[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]2[CH:13]([N:11]([CH3:10])[CH3:12])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 7806p-BromochlorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 111722992-(Dimethylaminophenylmethyl)cyclohexanone

Product 1

HCID 131723326HCID 131723326, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

0.63 g (25.9 mmole) of magnesium turnings was stirred in 10 ml of ether of analysis purity. 4.97 g (25.9 mmole) of 4-bromochlorobenzene dissolved in 30 ml of ether were added dropwise so that the reaction mixture boiled gently. After completion of the addition the reaction mixture was boiled for a further hour at RT. 5.0 g (21.6 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 40 ml of saturated ammonium chloride solution while cooling in an ice bath, and extracted three times at RT with in each case 100 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). 7.24 g of crude base (97.4% of theory) were obtained. 5.43 g of 1-(4-chlorophenyl)-2-(dimethylaminophenylmethyl)cyclohexanol, hydrochloride (66.0%) 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 175° C.

Workup

  1. additionwere added dropwise so that the reaction mixture
  2. additionAfter completion of the addition the reaction mixture
  3. waitwas boiled for a further hour at RT
  4. temperaturewhile cooling in an ice bath
  5. temperaturewhile cooling in an ice bath
  6. extractionextracted three times at RT with in each case 100 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. custom7.24 g of crude base (97.4% of theory) were obtained

Sources & evidence

ORD record
ord-7edbfb876ab145a4bc388fd965eea0c0
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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