Hexane → 3-(Bromomethyl)-5-fluoro-1-benzothiophene

HRID 1843941Notes

Reaction equation

HRID 1843941 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][CH:7]=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[Br:12]N1C(=O)CCC1=O.CCCCCC>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:9][C:8]1[C:4]2[CH:3]=[C:2]([F:1])[CH:11]=[CH:10][C:5]=2[S:6][CH:7]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 67184N-bromobutanimideHCID 5968285-Fluoro-3-methyl-benzo[b]thiophene

Product 1

HCID 136425923-(Bromomethyl)-5-fluoro-1-benzothiopheneYield 52%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

5-Fluoro-3-methyl-benzo[b]thiophene (1.7 g, 10.24 mmol) was reacted with N-bromo succinimide (2 g, 1126 mmol) and benzoyl peroxide (2 mg) in CCl4 (15 mL). The resulting reaction mass was refluxed using photoelectric radiation. The reaction was monitored by TLC (100% hexane). The reaction mass was quenched with water and separated the CCl4 layer. The aqueous layer was extracted with chloroform and the organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated. Purification by column chromatography on silica gel (100% hexane) afforded 1.3 g of the product (52% yield).

Workup

  1. customThe resulting reaction mass
  2. temperaturewas refluxed
  3. customThe reaction mass was quenched with water
  4. customseparated the CCl4 layer
  5. extractionThe aqueous layer was extracted with chloroform
  6. washthe organic layer was washed with water, brine solution
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated
  9. customPurification by column chromatography on silica gel (100% hexane)

Sources & evidence

ORD record
ord-f6941e4832b8422188152412034059b6
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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