1-Bromo-3-chloropropane → HCID 12831123, compound

HRID 1905741Notes

Reaction equation

HRID 1905741 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[OH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:5][CH2:4][CH2:3][CH2:2][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][C:11]2=[O:16]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 12831123HCID 12831123, compound

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

1-Bromo-3-chloropropane (17.3 g) is added to a stirred mixture of 4-hydroxyindanone (14.8 g), potassium carbonate (15.3 g) in DMF/water (150 ml/50 ml) and the reaction mixture stirred at RT for about 4 days. The reaction mixture is partitioned between water and methylene chloride and the organic layer is separated, dried, filtered and evaporated, affording a residue which is chromatographed on a silica gel column to yield the desired product as a white solid.

Workup

  1. customThe reaction mixture is partitioned between water and methylene chloride
  2. customthe organic layer is separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customaffording a residue which
  7. customis chromatographed on a silica gel column

Sources & evidence

ORD record
ord-3b074cb27257427da39f6055ddb11269
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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