Bromobenzene → HCID 13298046, compound

HRID 2309758Notes

Reaction equation

HRID 2309758 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:15][CH2:16][CH2:17][CH:18]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].[Cl-].[NH4+]>O1CCCC1>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:15][CH2:16][CH2:17][CH:18]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[OH:20]

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 13298045HCID 13298045, compound

Product 1

HCID 13298046HCID 13298046, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

First a Grignard complex is prepared under dry conditions by allowing 3.6 g of magnesium turnings in 25 ml of dry tetrahydrofuran to react with 23.6 g of bromobenzene in 50 ml of dry tetrahydrofuran. Then the evaporation residue obtained in step (a) in 75 ml of dry tetrahydrofuran is added. The reaction mixture is refluxed for 2 h. The cooled mixture is poured into a saturated solution of ammonium chloride. After shaking, the organic layer is separated. The extraction is repeated with ether. Then the organic layers are combined and dried over sodium sulfate. Finally the solvent is evaporated.

Workup

  1. customFirst a Grignard complex is prepared under dry conditions
  2. temperatureThe reaction mixture is refluxed for 2 h
  3. customthe organic layer is separated
  4. extractionThe extraction
  5. dry with materialdried over sodium sulfate
  6. customFinally the solvent is evaporated

Sources & evidence

ORD record
ord-881ea615fa0b4b139e679c3b659b1e30
Source dataset
uspto-grants-1987_09
Patent number
US04696949

Reaction notes

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