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

HRID 1069232노트

반응식

HRID 1069232 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

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): δ8.28 (d, 1H), 7.58-7.52 (m, 2H), 7.39-7.34 (m, 1H), 7.29 (d, 1H), 7.18 (dd, 1H), 7.14 and 7.13 (d, 1H), 3.18 (quintet, 1H), 2.44 (s, 3H), 2.40 (s, 3H), 2.06-2.02 (m, 2H), 1.75-1.45 (m containing a singlet at δ1.60, 9H); 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-94c874967c9441999c7b5aa3cdb4bb34
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251936B1

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