Bromine → HCID 10297816、化合物

HRID 1069238ノート

反応式

HRID 1069238 の反応式
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[C:19]([CH3:21])[C:18]([O:22][C:23](=[O:25])[CH3:24])=[C:17]([CH3:26])[CH:16]=4)[C:4]=2[C:3]=1[CH3:27])[CH:12]=[CH:11][CH:10]=[CH:9]3.[Br:28]Br>C(Cl)Cl>[Br:28][C:7]1[C:5]2[S:6][C:2]([CH3:1])=[C:3]([CH3:27])[C:4]=2[C:14]([C:15]2[CH:16]=[C:17]([CH3:26])[C:18]([O:22][C:23](=[O:25])[CH3:24])=[C:19]([CH3:21])[CH:20]=2)=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[CH:12]2

参加物

4

反応物 2

HCID 24408BromineHCID 10199432HCID 10199432、化合物

生成物 1

HCID 10297816HCID 10297816、化合物収率 55.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of acetic acid 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenyl ester (10.0 g, 26.7 mmol) and ferric chloride (0.23 g, 1.4 mmol) in anhydrous methylene chloride (231 mL) was placed at −78 C. under nitrogen. The reaction mixture was protected from light and a solution of bromine (1.5 mL, 29.4 mmol) in anhydrous methylene chloride (38 mL) was added dropwise over a period of 50 min. After 30 min the reaction was quenched with dilute sodium bisulfite, diluted with water, and the resulting mixture was extracted with diethyl ether. The diethyl ether layer was washed twice with water, brine, and then dried (MgSO4). Concentration under reduced pressure and chromatography with petroleum ether:ethyl acetate (97:3, then 95:5) gave the title compound as a white solid (6.7 g, 55%): NMR (DMSO-d6): δ8.27 (d, 1H), 7.60 (d, 1H), 7.56-7.52 (ddd, 1H), 7.38-7.34 (ddd, 1H), 7.06 (s, 2H), 2.43 (s, 3H), 2.41 (s, 3H), 2.22 (s, 6H), 1.64 (s, 3H); MS(EI): [M+], 1 bromine isotope pattern, 452/454; Anal. Calc. for C24H21BrO2S: C, 63.58; H, 4.67; N, 0.00. Found: C, 63.41; H, 4.45; N, 0.08.

後処理

  1. customAfter 30 min the reaction was quenched with dilute sodium bisulfite
  2. additiondiluted with water
  3. extractionthe resulting mixture was extracted with diethyl ether
  4. washThe diethyl ether layer was washed twice with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration under reduced pressure and chromatography with petroleum ether:ethyl acetate (97:3

出典と根拠

ORDレコード
ord-c5a5679f2c934ad0aae192d1c045485f
出典データセット
uspto-grants-2001_06
特許番号
US06251936B1

反応ノート

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