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

HRID 1496877노트

반응식

HRID 1496877 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.C(OCC)(=O)C.[BrH:25]>O>[Br:25][C:5]1[CH:7]=[C:8]([O:9][CH3:10])[C:2]([Cl:1])=[CH:3][C:4]=1[F:11]

참가 물질

7

반응물 5

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 1850824-Chloro-2-fluoro-5-methoxyanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 102203785-Bromo-2-chloro-4-fluoroanisole

시약·촉매·용매 1

HCID 962Water용매

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. After addition, methylene chloride (50 mL) and cupric bromide (30.0 g, 0.244 mol) were added slowly. The reaction mixture was then warmed to ambient temperature, stirred for one hour, filtered through a bed of celite, and extracted with methylene chloride (2×100 mL). The combined organic phases were dried 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. additionwere added slowly
  2. filtrationfiltered through a bed of celite
  3. extractionextracted with methylene chloride (2×100 mL)
  4. customThe combined organic phases were dried
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-691402f0ce7c48a28be288f4ad9122bf
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199943B2

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