Thionyl Chloride → 2-Bromo-6-[(3-fluoro-4-methoxybenzoyl)amino]-4-methoxyphenyl 3-fluoro-4-methoxybenzoate

HRID 491728ノート

反応式

HRID 491728 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[NH2:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([Br:26])[C:19]=1O>C(OCC)C.N1C=CC=CC=1.C(Cl)Cl.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][C:19]1[C:18]([NH:17][C:5](=[O:6])[C:4]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([F:1])[CH:3]=2)=[CH:23][C:22]([O:24][CH3:25])=[CH:21][C:20]=1[Br:26])=[O:6]

参加物

8

反応物 3

HCID 24386Thionyl ChlorideHCID 27334013-Fluoro-4-methoxybenzoic acidHCID 111719822-Amino-6-Bromo-4-Methoxyphenol

生成物 1

HCID 111799682-Bromo-6-[(3-fluoro-4-methoxybenzoyl)amino]-4-methoxyphenyl 3-fluoro-4-methoxybenzoate収率 97.1%

試薬・触媒・溶媒 4

HCID 1049Pyridine溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-fluoro-4-methoxybenzoic acid (39.0 g, 229 mmol), thionyl chloride (100 mL), and N,N-dimethylformamide (0.5 mL) was refluxed for 1 h. The volatiles were removed under vacuum. The solids were taken in benzene (twice) and the volatiles were removed under vacuum. The residue was dissolved in CH2Cl2 (100 mL) and added into a cold (0° C.) mixture (mechanically stirred) of 2-amino-6-bromo-4-methoxyphenol (20.0 g, 91.7 mmol) and CH2Cl2 (150 mL). Anhydrous pyridine (37.0 mL, 468.5 mmol) was added dropwise into the new mixture. During the pyridine addition a precipitate was formed. The mixture was stirred for 30 min and then ethyl ether (250 mL) was added. The precipitated solids were filtered off and washed with ethyl ether. The solids were taken in water and stirred for 20 min. The solids were then filtered off and dried to give an off-white solid (46.5 g, 97% yield, m.p. 184-186° C.); MS m/e 520 (M−H)+.

後処理

  1. temperaturewas refluxed for 1 h
  2. customThe volatiles were removed under vacuum
  3. customwere removed under vacuum
  4. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  5. additionadded into a cold (0° C.) mixture (
  6. customwas formed
  7. filtrationThe precipitated solids were filtered off
  8. washwashed with ethyl ether
  9. stirringstirred for 20 min
  10. filtrationThe solids were then filtered off
  11. customdried

出典と根拠

ORDレコード
ord-6dd9141d8f7c4b17afcbe718773b26fb
出典データセット
uspto-grants-2009_05
特許番号
US07531564B2

反応ノート

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