Dimethylformamide → Dibenzo(b,d)thiophene-2-carbaldehyde

HRID 594284

反応式

HRID 594284 の反応式
Br[C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[Li]CCCC.CN([CH:23]=[O:24])C.[NH4+].[Cl-]>CCOCC>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[S:6][C:5]=2[CH:13]=[CH:14][C:2]=1[CH:23]=[O:24]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 2995082-BromodibenzothiopheneHCID 178418339Butyllithium

生成物 1

HCID 641360Dibenzo(b,d)thiophene-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

A cooled (0° C.) suspension of commercially available 2-bromodibenzo[b,d]thiophene (500 mg; 1.90 mmol) in anh. Et2O (5 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.26 ml; 2.01 mmol). The resulting suspension was further stirred at 0° C. for 30 min. Anh. DMF (0.156 ml; 2.03 mmol) was then added, and the mixture was stirred at rt for 20 min. Aq. sat. NH4Cl and Et2O were successively added, and the aq. layer was further extracted with Et2O. The mixed organic layers were washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM) afforded dibenzo[b,d]thiophene-2-carbaldehyde as an off-white solid. LC-MS (conditions A): tR=0.87 min.; no ionisation.

後処理

  1. temperatureA cooled
  2. stirringthe mixture was stirred at rt for 20 min
  3. extractionthe aq. layer was further extracted with Et2O
  4. washThe mixed organic layers were washed with water
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM)

出典と根拠

ORDレコード
ord-7ac324d6fe2c4573bcdca021ee6c52fc
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

関連ノート

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