Sodium Carbonate → 2-Chloro-4-(5-chloro-2-methoxyphenyl)benzoic acid

HRID 16090

反応式

HRID 16090 の反応式
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([O:22][CH3:23])=[C:17]([CH:21]=1)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[Cl:11][C:4]1[CH:3]=[C:2]([C:15]2[CH:14]=[C:13]([Cl:12])[CH:21]=[CH:17][C:16]=2[O:22][CH3:23])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 769705-Chloro-o-anisic acidHCID 1088294-Bromo-2-chlorobenzoic acid

生成物 1

HCID 532275772-Chloro-4-(5-chloro-2-methoxyphenyl)benzoic acid収率 79.2%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 887Methanol溶媒

実験手順

4-bromo-2-chlorobenzoic acid (0.4 g), 5-chloro-2-methoxybenzoic acid (0.4 g), Pd(dppf)Cl2 (0.12 g), sodium carbonate (0.9 g), dioxan (15 ml) and methanol (5 ml) were charged to a flask and heated at reflux for 16 h. Cooled to room temp and filtered (hyflo). The filtrate was concentrated in vacuo, then dissolved in ethyl acetate. The suspension was made basic by addition of dilute NaOH. The aqueous layer was separated and acidified using 2M HCl, extracted with EtOAc, dried (MgSO4) and evaporated in vacuo to give the sub-title compound Yield 0.4 g

後処理

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered (hyflo)
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutiondissolved in ethyl acetate
  6. additionThe suspension was made basic by addition of dilute NaOH
  7. customThe aqueous layer was separated
  8. extractionextracted with EtOAc
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-ab2b160fe763407f91689f6ef0679c8c
出典データセット
uspto-grants-2010_06
特許番号
US07737135B2

関連ノート

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