Sodium Carbonate → 2-Bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one

HRID 241450

반응식

HRID 241450 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.[Br:15]Br.C(=O)([O-])[O-].[Na+].[Na+]>Br.C(O)(=O)C.O.CCOC(C)=O>[Br:15][CH:10]([CH3:11])[C:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:13])([F:14])[F:1])=[CH:8][CH:7]=1)=[O:12]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 136554p-Trifluoromethylpropiophenone

생성물 1

HCID 104238192-Bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one수율 106.4%

시약·촉매·용매 4

HCID 176Acetic Acid용매2회HCID 260Hydrogen Bromide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Dissolve p-trifluoromethylpropiophenone (5.130 g, 25.120 mmol) in hydrogen bromide (30.00 mL) and acetic acid (20 mL). Add bromine (1.23 mL, 23.864 mmol) in acetic acid (25 mL) drop-wise over 30 minutes. Stir the reaction mixture for 48 hours, and dilute the reaction mixture with water (1 L) and EtOAc (250 mL). Add solid sodium carbonate portion-wise to adjust the pH to ˜7 allowing the gas evolution to cease between additions. Extract the resulting mixture with EtOAc (2×250 mL). Dry the organic extracts over Na2SO4. Filter; collect the filtrate; and concentrate the filtrate under reduced pressure to give the title compound as a clear oil (7.140 g, 100% crude yield). 1H NMR (399.83 MHz, d6-DMSO) δ 8.20 (dd, J=0.7, 8.8 Hz, 2H), 7.92-7.90 (m, 2H), 5.85 (q, J=6.5 Hz, 1H), 1.78 (d, J=6.5 Hz, 3H).

후처리

  1. extractionExtract the resulting mixture with EtOAc (2×250 mL)
  2. dry with materialDry the organic extracts over Na2SO4
  3. filtrationFilter
  4. customcollect the filtrate
  5. concentrationand concentrate the filtrate under reduced pressure

출처 및 근거

ORD 기록
ord-59ad1ff4512c4a8bb900345bf07d31e4
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648200B2

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