Bromine → HCID 68181387, compound

HRID 331383Notes

Reaction equation

HRID 331383 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[C:11](=[O:20])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[Br:21]Br>C(Cl)Cl.O>[Br:21][C:10]1[C:11](=[O:20])[C:12]2[C:17]([C:9]=1[C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=1)=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2

Participants

5

Reactant 2

HCID 24408BromineHCID 70310610HCID 70310610, compound

Product 1

HCID 68181387HCID 68181387, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(3,5-difluorophenyl)-5-methoxy-1H-inden-1-one (810 mg, 2.98 mmol) obtained in Step 2 in CH2Cl2 (10 mL) at 0° C. was added dropwise a solution of Br2 (571 mg, 3.57 mmol) in CH2Cl2 (3 mL). The mixture was stirred for 3 h at room temperature. The reaction was diluted with H2O (10 mL) and extracted with CH2Cl2. The extracts were washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (CH2Cl2/hexanes) to afford the desired product (1.0 g, 95%).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe extracts were washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-c988d95f4db44b89b70278ee82944418
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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