Bromine → HCID 10297816, 화합물

HRID 1069238노트

반응식

HRID 1069238 반응식
[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

참가 물질

4

반응물 2

HCID 24408BromineHCID 10199432HCID 10199432, 화합물

생성물 1

HCID 10297816HCID 10297816, 화합물수율 55.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c5a5679f2c934ad0aae192d1c045485f
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251936B1

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