Ammonium Chloride → HCID 178447899, compound

HRID 1245269

Reaction equation

HRID 1245269 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1Br.[Mg].[CH2:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([CH:20]2[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)[CH2:16][CH2:15]1)[CH2:12][CH3:13].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:23]1([OH:26])[CH2:22][CH2:21][CH:20]([C@H:17]2[CH2:18][CH2:19][C@H:14]([CH2:11][CH2:12][CH3:13])[CH2:15][CH2:16]2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 678622-Bromo-1,4-difluorobenzeneHCID 5462224MagnesiumHCID 178447904HCID 178447904, compound

Product 1

HCID 178447899HCID 178447899, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 2,5-difluorobromobenzene (1.33 mmol) in THF (10 ml) is added dropwise to magnesium (1.44 mmol). After the addition is completed, the reaction mixture is stirred at 50° C. for 2 hrs. To the reaction mixture, a solution of 4-(trans-4-propylcyclohexyl)cyclohexanone (1.03 mmol) in THF (10 ml) is added dropwise. After the addition is completed, the reaction mixture is stirred for 2 hrs at 50° C. A saturated aqueous solution of ammonium chloride (10 ml) is added in small portions and the aqueous layer is extracted with ethyl acetate (100 ml) twice. The extract is washed with water, and then dried over anhydrous magnesium sulfate. The titled compound is obtained by evaporation of the solvent under reduced pressure.

Workup

  1. additionAfter the addition
  2. additionAfter the addition
  3. stirringthe reaction mixture is stirred for 2 hrs at 50° C
  4. extractionthe aqueous layer is extracted with ethyl acetate (100 ml) twice
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-becb4e41da5b4a20ad9f930593b35783
Source dataset
uspto-grants-2006_10
Patent number
US07125589B1

Linked notes

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