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Hydrochloric Acid → 3'-Borono-4-chlorobiphenyl-3-carboxylic acid

HRID 404960
ノート
印刷プレビュー

反応式

HRID 404960 の反応式
B([C:4]1[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])(O)O.I[C:15]1[CH:16]=[C:17]([B:21]([OH:23])[OH:22])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].Cl>C1(C)C=CC=CC=1.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[B:21]([C:17]1[CH:16]=[C:15]([C:4]2[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([C:9]([OH:11])=[O:10])[CH:12]=2)[CH:20]=[CH:19][CH:18]=1)([OH:23])[OH:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27343623-Iodophenylboronic acidHCID 230053332-Chloro-5-(dihydroxyboranyl)benzoic acid

生成物 1

HCID 667994763'-Borono-4-chlorobiphenyl-3-carboxylic acid

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 21867641Toluene methanol溶媒

反応条件

温度
75 °C

実験手順

5-Borono-2-chlorobenzoic acid (200 mg, 1 mmol), 3-iodophenylboronic acid (125 mg, 0.5 mmol), K2CO3 (207 mg, 1.5 mmol) and PdCl2(PPh3)2 (37 mg, 0.05 mmol) were dissolved in a mixture of toluene-MeOH (17 mL:1.7 mL) and heated at 75° C. for 3 hours. The mixture was filtered through celite washed with water and the solvent was evaporated in vacuo. The formed crude residue was acidified with 2 M HCl and extracted into EtOAc and dried over anhyd. Na2SO4, evaporated solvent in vacuo to obtain crude 3′-borono-4-chlorobiphenyl-3-carboxylic acid as a reddish brown solid. The crude product was used for the next step without further purification.

後処理

  1. filtrationThe mixture was filtered through celite
  2. washwashed with water
  3. customthe solvent was evaporated in vacuo
  4. customThe formed crude residue
  5. extractionextracted into EtOAc
  6. customdried over anhyd
  7. customNa2SO4, evaporated solvent in vacuo

出典と根拠

ORDレコード
ord-918fe80fdb5443108331e3c160e6302e
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748632B2

反応ノート

読み込み中…

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