Water → HCID 23114102, compound

HRID 2376374Notes

Reaction equation

HRID 2376374 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=3[S:12][CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br:21]Br.O>ClCCl.[Fe]>[Br:21][C:16]1[C:17]([CH3:19])=[CH:18][C:13]2[S:12][CH2:11][CH:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)[C:14]=2[C:15]=1[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 23113913HCID 23113913, compound

Product 1

HCID 23114102HCID 23114102, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothiophene synthesized in Reference Example 212 (4.45 g, 15.8 mmol) and iron powder (59 mg, 1.05 mmol) in dichloromethane (20 mL) was added bromine (0.81 mL, 15.8 mmol) at 0° C., and the mixture was stirred at the same temperature for 1 hour. Water was poured into the reaction mixture, which was extracted with ethyl acetate. The extract was washed with a saturated sodium hydrogen carbonate solution and water, was dried over magnesium sulfate, was filtered and then was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10) to obtain 4.6 g (yield 80%) of the title compound. Melting point: 98-100° C. (hexane-ethyl acetate).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with a saturated sodium hydrogen carbonate solution and water
  3. dry with materialwas dried over magnesium sulfate
  4. filtrationwas filtered
  5. concentrationwas concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-de4758a97f534573b2dd038412e4eb07
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

Loading…