Allyl bromide → HCID 15096989, compound

HRID 345517Notes

Reaction equation

HRID 345517 reaction equation
[CH3:1][C:2](=O)[CH3:3].C(=O)=O.BrCC=C.[Mg].[CH:13]1([C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[O:17])[CH2:15][CH2:14]1.[Cl-].[NH4+]>O(CC)CC>[CH:13]1([C:16]([CH2:3][CH:2]=[CH2:1])([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[OH:17])[CH2:14][CH2:15]1

Participants

7

Reactant 5

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 69876Cyclopropyl 4-fluorophenyl ketoneHCID 5462224MagnesiumHCID 18522661Acetone cardice

Product 1

HCID 15096989HCID 15096989, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred and cooled (2-propanone/CO2 -bath)Grignard complex previously prepared starting from 254.1 parts of 3-bromo-1-propene, 54.7 parts of magnesium and 1540 parts of anhydrous 1,1'-oxybisethane was added dropwise, during a 1 hour-period, a solution of 330 parts of cyclopropyl (4-fluorophenyl)methanone in 280 parts of anhydrous 1,1'-oxybisethane at a temperature below -5° C. The reaction mixture was allowed to reach room temperature and stirring was continued overnight at room temperature. The mixture was cooled to 0° C. and decomposed with 350 parts of a saturated ammonium chloride solution. The 1,1'-oxybisethane was decanted and the residual salts were suspended twice in 140 parts of 1,1'-oxybisethane. The latter was decanted and the combined 1,1'-oxybisethane-phases were washed with 500 parts of water. The organic phase was dried, filtered and evaporated. From the residue, the forerun was distilled off by "Spinning Band". The distillation residue yielded 255.7 parts (62 %) of α-cyclopropyl-4-fluoro-α-(2-propenyl)benzenemethanol (intermediate 1).

Workup

  1. custompreviously prepared
  2. additionwas added dropwise, during a 1 hour-period
  3. customat a temperature below -5° C
  4. customto reach room temperature
  5. stirringstirring
  6. customThe 1,1'-oxybisethane was decanted
  7. customThe latter was decanted
  8. washthe combined 1,1'-oxybisethane-phases were washed with 500 parts of water
  9. customThe organic phase was dried
  10. filtrationfiltered
  11. customevaporated
  12. distillationFrom the residue, the forerun was distilled off by "

Sources & evidence

ORD record
ord-babbc01cbef54637af8007247e1a97bd
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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