Diethyl Ether → HCID 14990578, compound

HRID 2248317Notes

Reaction equation

HRID 2248317 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[Mg].O(CC)CC.[CH3:15][N:16]1[C:20]2[C:21]([CH:25]=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1>O>[F:8][C:4]1[CH:3]=[C:2]([CH:25]([C:21]2[C:20]3[N:16]([CH3:15])[N:17]=[N:18][C:19]=3[CH:24]=[CH:23][CH:22]=2)[OH:26])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 140821-Bromo-3-fluorobenzeneHCID 5462224MagnesiumHCID 14990577HCID 14990577, compound

Product 1

HCID 14990578HCID 14990578, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and refluxed Grignard complex, previously prepared starting from 8.15 parts of 1-bromo-3-fluorobenzene, 1.2 parts of magnesium and a small amount of 1,1'-oxybisethane was added a solution of 5 parts of 1-methyl-1H-benzotriazole-7-carboxaldehyde in 80 parts of 1,1'-oxybisethane. After stirring for 2 hours at room temperature, the reaction mixture was poured into 300 parts of water. The product was extracted three times with 65 parts of dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was stirred for 15 minutes in 100 parts of water and 13 parts of petroleum ether at room temperature. The product was filtered off and dried, yielding 7.6 parts (95.2%) of α-(3-fluorophenyl)-1-methyl-1H-benzotriazole-7-methanol; mp. 152° C. (int. 19).

Workup

  1. temperaturerefluxed Grignard complex
  2. custompreviously prepared
  3. stirringAfter stirring for 2 hours at room temperature
  4. extractionThe product was extracted three times with 65 parts of dichloromethane
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe residue was stirred for 15 minutes in 100 parts of water and 13 parts of petroleum ether at room temperature
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-d1874682b2584f7fb887a22e80347d48
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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