Water → 5-Bromo-4,4'-didodecyl-2,2'-bithiophene

HRID 1257980ノート

反応式

HRID 1257980 の反応式
[CH2:1]([C:13]1[CH:14]=[C:15]([C:18]2[S:19][CH:20]=[C:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:22]=2)[S:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C1C(=O)N([Br:42])C(=O)C1.O>C(Cl)(Cl)Cl.CC(O)=O>[Br:42][C:20]1[S:19][C:18]([C:15]2[S:16][CH:17]=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:14]=2)=[CH:22][C:21]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 219172654,4'-Didodecyl-2,2'-bithiophene

生成物 1

HCID 671208205-Bromo-4,4'-didodecyl-2,2'-bithiophene収率 85%

試薬・触媒・溶媒 1

HCID 21584526Acetic acid chloroform溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4,4′-didodecyl-2,2′-bithiophene (0.100 g, 0.199 mmol) in CHCl3/HOAc (1:1) (Vt=2.0 mL) at 0° C. was added N-bromosuccimide (NBS, 35.7 mg, 0.199 mmol) in portions over a period of 45 minutes. The reaction mixture was stirred for 1 hour at 0° C. and overnight at room temperature. The reaction mixture was poured into water (50.0 mL) and extracted with chloroform (3×50.0 mL). The combined organic phases were washed with water (50.0 mL), NaOH solution, and dried over MgSO4. After filtration through Celite, the filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexanes) to provide 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A) as a colorless oil (98.0 mg, 85% yield). 1H NMR (CDCl3): δ 0.84-1.54 (m, 46H), 2.57 (m, 4H), 6.81 (s, 1H), 6.84 (s, 1H), 6.94 (s, 1H).

後処理

  1. extractionextracted with chloroform (3×50.0 mL)
  2. washThe combined organic phases were washed with water (50.0 mL), NaOH solution
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration through Celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by column chromatography on silica gel (hexanes)

出典と根拠

ORDレコード
ord-76cd16eac47841e4bc50a1a442274da4
出典データセット
uspto-grants-2013_06
特許番号
USRE044304E1

反応ノート

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