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

HRID 1782592ノート

反応式

HRID 1782592 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 102203785-Bromo-2-chloro-4-fluoroanisole収率 49%

試薬・触媒・溶媒 3

HCID 260Hydrogen Bromide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9e31a094b5ad4c52a5d3d502c4b2d626
出典データセット
uspto-grants-2009_03
特許番号
US07498468B2

反応ノート

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