Bromobenzene → HCID 21555791, compound

HRID 267219Notes

Reaction equation

HRID 267219 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].C1([Mg]Br)C=CC=CC=1.[C:17]([C:25]1[O:29][N:28]=[C:27]([CH3:30])[CH:26]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[C:2]1([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:25]2[O:29][N:28]=[C:27]([CH3:30])[CH:26]=2)[OH:24])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 3184485-benzoyl-3-methylisoxazoleHCID 5462224MagnesiumHCID 178418255HCID 178418255, compound

Product 1

HCID 21555791HCID 21555791, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

From 31.4 grams (0.2 mole) bromobenzene and 4.86 grams (0.2 mole) magnesium turnings in 150 ml ether there was prepared a solution of phenylmagnesium bromide which was added dropwise at -5°C to a solution of 18.7 grams (0.1 mole) 5-benzoyl-3-methylisoxazole. Heating was effected slowly, followed by boiling under reflux for one hour and poured onto ice. After acidification with 25 ml hydrochloric acid, the ethereal phase was separated; washing with bicarbonate solution was effected, followed by drying and concentration. The residue was crystallized with ether/petroleum ether. 21 grams bis-phenyl-(3-methylisoxazol-5-yl)-carbinol of the melting point 116°-118°C. were obtained.

Workup

  1. temperatureHeating
  2. temperatureunder reflux for one hour
  3. additionpoured onto ice
  4. customAfter acidification with 25 ml hydrochloric acid, the ethereal phase was separated
  5. washwashing with bicarbonate solution
  6. customby drying
  7. concentrationconcentration
  8. customThe residue was crystallized with ether/petroleum ether

Sources & evidence

ORD record
ord-92ea336392fe41b1a02dc9f8e34fa0b9
Source dataset
uspto-grants-1976_03
Patent number
US03941800

Reaction notes

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