Bromine → Acetic acid 2-cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester

HRID 1954267ノート

反応式

HRID 1954267 の反応式
[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[C:24]4[C:23]([CH3:25])=[C:22]([CH3:26])[S:21][C:20]=4[CH:19]=[C:18]4[C:13]=3[CH:14]=[CH:15][CH:16]=[CH:17]4)[CH:9]=[CH:8][C:7]=2[O:27][C:28](=[O:30])[CH3:29])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:31]Br>C(Cl)Cl>[CH:1]1([C:6]2[CH:11]=[C:10]([C:12]3[C:24]4[C:23]([CH3:25])=[C:22]([CH3:26])[S:21][C:20]=4[C:19]([Br:31])=[C:18]4[C:13]=3[CH:14]=[CH:15][CH:16]=[CH:17]4)[CH:9]=[CH:8][C:7]=2[O:27][C:28](=[O:30])[CH3:29])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

4

反応物 2

HCID 24408BromineHCID 53716940Acetic acid 2-cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester

生成物 1

HCID 54419856Acetic acid 2-cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To acetic acid 2-cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenyl ester (2.9 g, 7.7 mmol) in anhydrous methylene chloride (68 mL) was added ferric chloride (66 mg, 0.41 mmol). The reaction mixture was placed under nitrogen and cooled to -78° C. The reaction mixture was protected from light and a solution of bromine (0.44 mL, 8.5 mmol) in anhydrous methylene chloride (11 mL) was added dropwise over a period of 15 min. After stirring at -78° C. for 45 min the reaction was quenched with dilute sodium bisulfite, and then poured into water (200 ML). The resulting mixture was extracted with diethyl ether (300 mL), and the diethyl ether layer was washed with water and then brine. Concentration under reduced pressure and chromatography with petroleum ether:ethyl acetate (95:5) gave the title compound as a white solid (2.7 g, 79%): (CDCl3): δ 8.28 (d, 1 H), 7.58-7.52 (m, 2 H), 7.39-7.34 (m, 1 H), 7.29 (d, 1 H), 7.18 (dd, 1 H), 7.14 and 7.13 (d, 1 H), 3.18 (quintet, 1 H 2.44 (s, 3 H), 2.40 (s, 3 H), 2.06-2.02 (m, 2 H), 1.75-1.45 (m containing a singlet at δ 1.60, 9 H). MS(EI), [M+], 1 bromine isotope pattern, 492/494; Anal. Calc. for C27H25BrO2S: C, 65.72, H, 5.11, N, 0.00. Found: C, 63.18, H, 4.96, N, 0.00.

後処理

  1. customwas quenched with dilute sodium bisulfite
  2. additionpoured into water (200 ML)
  3. extractionThe resulting mixture was extracted with diethyl ether (300 mL)
  4. washthe diethyl ether layer was washed with water
  5. concentrationConcentration under reduced pressure and chromatography with petroleum ether:ethyl acetate (95:5)

出典と根拠

ORDレコード
ord-1a22e88609b1425b9081b4a0a32d7acd
出典データセット
uspto-grants-2000_09
特許番号
US06121271

反応ノート

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