Ammonia → 4-Bromo-3,5-dichlorobenzaldehyde

HRID 587782ノート

反応式

HRID 587782 の反応式
[Br:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[Cl:13].C(ON=O)(C)(C)C.NC1C(Cl)=CC(C(OC)=O)=CC=1Cl.N>CC#N>[Br:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[Cl:13]

参加物

6

反応物 4

HCID 222AmmoniaHCID 10906Tert-Butyl nitriteHCID 604808Methyl 4-amino-3,5-dichlorobenzoateHCID 508496864-Bromo-3,5-dichloro-benzoic acid methyl ester

生成物 1

HCID 224210974-Bromo-3,5-dichlorobenzaldehyde

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Methyl 4-bromo-3,5-dichlorobenzoate: CuBr2 (7.5 g, 34.08 mmol) in MeCN (50 mL) was stirred at 80° C. for 30 min. To this solution tert-butylnitrite (6.5 mL, 54.55 mmol) was added dropwise at the same temperature and the mixture was stirred for another 10 min. Methyl 4-amino-3,5-dichlorobenzoate in MeCN (30 mL) was added dropwise to the reaction mixture which was then stirred at 80° C. for 30 min. The reaction mixture was brought to ambient temperature. Aqueous ammonia solution (20 mL) was added and extracted with petroleum ether. The organic layer was washed with brine followed by water. The organic solution was dried (Na2SO4), filtered and concentrated to afford the title compound as an off white solid (7.5 g, 77%): 1H NMR (300 MHz, DMSO-d6) δ 8.02 (s, 2H), 3.94 (s, 3H); ESIMS m/z 282 ([M]+); IR (thin film) 1733, 762, 514 cm−1.

後処理

  1. stirringwas then stirred at 80° C. for 30 min
  2. customwas brought to ambient temperature
  3. extractionextracted with petroleum ether
  4. washThe organic layer was washed with brine
  5. dry with materialThe organic solution was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c5bd742776c54ec0a7ffe5bcc619d108
出典データセット
uspto-grants-2016_01
特許番号
US09226501B2

反応ノート

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