Bromobenzene → HCID 22504545, compound

HRID 1368942Notes

Reaction equation

HRID 1368942 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[CH:16][CH:15]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([C:26]1[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=1)[C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])=[CH:16][CH:15]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[OH:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 22504616HCID 22504616, compound

Product 1

HCID 22504545HCID 22504545, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Benzyloxy-2-(4-chlorophenyl)-1-[4-(2-dimethylaminoethoxy)phenyl]butan-1-one (9.4 g, 0.021 mol) is added to Grignard reagent prepared from bromobenzene (13.1 g, 0.083 mol) and Mg turnings (2.0 g, 0.083 mol) in dry tetrahydrofuran. The mixture is refluxed for 3 h. Saturated ammonium chloride solution is added to the cooled reaction mixture, the THF layer is separated and the aqueous phase is extracted with toluene. The combined organic phases are washed with water and the solvents are evaporated. The residual product (10.7 g) is used in the next reaction step without further purification.

Workup

  1. temperatureThe mixture is refluxed for 3 h
  2. customthe THF layer is separated
  3. extractionthe aqueous phase is extracted with toluene
  4. washThe combined organic phases are washed with water
  5. customthe solvents are evaporated
  6. customThe residual product (10.7 g) is used in the next reaction step without further purification

Sources & evidence

ORD record
ord-847584165ed346478c10fd9209aae608
Source dataset
uspto-grants-2003_06
Patent number
US06576645B1

Reaction notes

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