Bromine → 6-Bromo-3,4-dihydro-4,4,5,8-tetramethyl-2H-1-benzothiopyran

HRID 1839869

反応式

HRID 1839869 の反応式
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[CH:9][C:10]=2[CH3:12])[S:5][CH2:4][CH2:3]1.[Br:15]Br.S([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[C:9]([Br:15])[C:10]=2[CH3:12])[S:5][CH2:4][CH2:3]1

参加物

5

反応物 3

HCID 24408BromineHCID 129936844,4,5,8-TetramethylthiochromanHCID 23665763Sodium Bisulfite

生成物 1

HCID 129936856-Bromo-3,4-dihydro-4,4,5,8-tetramethyl-2H-1-benzothiopyran収率 87.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

100 ml of methylene chloride was added to 13.2 g (0.064 mol) of 4,4,5,8-tetramethylthiochroman, 10.2 g (0.064 mol) of bromine was dropwise added at room temperature, and then the mixture was allowed to react for 2 hours. After the completion of the reaction, 70 ml of a 2% sodium hydrogensulfite aqueous solution was added, excessive bromine was removed, and the reaction mixture was liquid-separated. An organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The methylene chloride was distilled off under reduced pressure, and the resultant oily substance was purified by silica gel column chromatography to give 15.9 g (yield 87%) of 4,4,5,8-tetramethyl-6-bromothiochroman.

後処理

  1. additionwas dropwise added at room temperature
  2. customto react for 2 hours
  3. additionwas added
  4. customexcessive bromine was removed
  5. customthe reaction mixture was liquid-separated
  6. washAn organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe methylene chloride was distilled off under reduced pressure
  9. customthe resultant oily substance was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-2d6e67dc71c441dcaed5ce03aff4a171
出典データセット
uspto-grants-2004_01
特許番号
US06677460B1

関連ノート

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