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Acetyl chloride → HCID 58764041, 화합물

HRID 2387025
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HRID 2387025 반응식
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[Br:12][C:13]1[C:18]([O:19][CH2:20][CH3:21])=[CH:17][C:16]([OH:22])=[C:15]([CH2:23][CH3:24])[CH:14]=1>C(Cl)Cl>[Br:12][C:13]1[C:18]([O:19][CH2:20][CH3:21])=[CH:17][C:16]([O:22][C:1](=[O:3])[CH3:2])=[C:15]([CH2:23][CH3:24])[CH:14]=1
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참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58764135HCID 58764135, 화합물

생성물 1

HCID 58764041HCID 58764041, 화합물수율 53.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Acetyl chloride (0.91 mL, 12.8 mmol) followed by triethylamine (1.8 mL, 12.8 mmol) were added to a stirred solution of 4-bromo-5-ethoxy-2-ethyl-phenol (2.6 g, 10.7 mmol) dissolved in CH2Cl2 (20 mL). The reaction was stirred for 45 mins and then partitioned between 1N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine dried over Na2SO4 and concentrated. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) gave the product as a clear oil (1.64 g, 53%). 1H NMR (400 MHz, CDCl3): δ 1.16 (t, J=7.6 Hz, 3 H), 1.45 (t, J=7.1 Hz, 3 H), 2.31 (s, 3 H), 2.45 (q, J=7.6 Hz, 2 H), 4.05 (q, J=7.1 Hz, 2 H), 6.58 (s, 1 H), 7.41 (s, 1 H).

후처리

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-9ec0ff261cb3477eac8bcb0793422b52
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08268835B2

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