Bromobenzene → [2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-phenyl-methanol

HRID 2297409Notes

Reaction equation

HRID 2297409 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][C:10]1([CH3:25])[CH2:14][O:13][C:12]([C:15]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:16]=2[CH:17]=[O:18])=[N:11]1>C(OCC)C.C(Br)C.BrCCBr>[CH3:9][C:10]1([CH3:25])[CH2:14][O:13][C:12]([C:15]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:16]=2[CH:17]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[OH:18])=[N:11]1

Participants

7

Reactant 3

HCID 7961BromobenzeneHCID 5462224MagnesiumHCID 122201362-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehyde

Product 1

HCID 12856168[2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-phenyl-methanolYield 107.8%

Reagents, catalysts & solvents 3

HCID 6332Ethyl BromideCatalystHCID 78391,2-DibromoethaneCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Magnesium turnings for Grignard (0.12 g, 4.71 mmoles) in ethyl ether (8 ml) were put under N2 and stirring at room temperature. Ethyl bromide (2 drops) and then, slowly, bromobenzene (0.52 ml, 4.93 mmoles) in ethyl ether (10 ml) and 1,2-dibromoethane (2 drops) were added. The temperature arose to reflux and was kept as such for 1 hour. The mixture was treated with 2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-benzaldehyde (1 g, 4.29 mmoles), prepared as described in example 2, and kept at reflux for a further hour, then cooled, poured into water/ice and extracted more times with ethyl acetate. The organic phases were washed with water, anhydrified and brought to dryness to give 1.44 g of the title compound (yield: 98%).

Workup

  1. temperatureto reflux
  2. customsuch for 1 hour
  3. customprepared
  4. temperatureat reflux for a further hour
  5. temperaturecooled
  6. extractionextracted more times with ethyl acetate
  7. washThe organic phases were washed with water

Sources & evidence

ORD record
ord-dacfcc6caaab4793a1ea3cddb345f7f3
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

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