Bromide ion → 5-Bromo-2-chloro-4-fluoroanisole

HRID 1782592노트

반응식

HRID 1782592 반응식
[Cl:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][C:5](N)=[C:4]([F:11])[CH:3]=1.N([O-])=O.[Na+].C(Cl)Cl.[Br-:19]>Br.O.C(OCC)(=O)C>[Br:19][C:5]1[CH:7]=[C:8]([O:9][CH3:10])[C:2]([Cl:1])=[CH:3][C:4]=1[F:11]

참가 물질

8

반응물 4

HCID 259Bromide ionHCID 6344DichloromethaneHCID 1850824-Chloro-2-fluoro-5-methoxyanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 102203785-Bromo-2-chloro-4-fluoroanisole수율 49%

시약·촉매·용매 3

HCID 260Hydrogen Bromide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-chloro-2-fluoro-5-methoxyaniline (25.0 g, 0.143 mol) in 10% HBr (250 mL) was cooled to 0° C. and a solution of sodium nitrite (15.0 g, 0.218 mol) in water (20 mL) was slowly added. Methylene chloride (50 mL) and curpric bromide (30.0 g, 0.244 mol) were added slowly and then the mixture was warmed to ambient temperature and stirred for 1 hour. The reaction mixture was filtered through a bed of celite and extracted with methylene chloride (2×100 mL) and the combined organic phases were dried (sodium sulfate) and concentrated. Chromatography of the dark oil (5% ethyl acetate in hexanes) gave 1-bromo-4-chloro-2-fluoro-5-methoxybenzene (16.6 g, 0.070 mol): 1H NMR (CDCl3): δ 7.20 (m, 1H) 7.05 (dd, 1H), 4.00 (s, 3H).

후처리

  1. filtrationThe reaction mixture was filtered through a bed of celite and
  2. extractionextracted with methylene chloride (2×100 mL)
  3. dry with materialthe combined organic phases were dried (sodium sulfate)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9e31a094b5ad4c52a5d3d502c4b2d626
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498468B2

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