5-Bromosalicylic acid → 3'-Chloro-4'-fluoro-4-hydroxy-biphenyl-3-carboxylic acid

HRID 2373782ノート

反応式

HRID 2373782 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[F:8].Br[C:13]1[CH:14]=[CH:15][C:16]([OH:22])=[C:17]([CH:21]=1)[C:18]([OH:20])=[O:19].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([OH:22])=[C:17]([C:18]([OH:20])=[O:19])[CH:21]=2)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

6

反応物 3

HCID 69725-Bromosalicylic acidHCID 10340Sodium CarbonateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)

生成物 1

HCID 219213173'-Chloro-4'-fluoro-4-hydroxy-biphenyl-3-carboxylic acid収率 43.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

3-Chloro-4-fluoro-phenylboronic acid (3.2 g, 18.4 mmol), 5-bromo-2-hydroxy-benzoic acid (4.0 g, 18.4 mmol), and Pd (PPh3)4 (1.67 g, 1.84 mmol) were dissolved in 250 mL of DME, a 1 M Na2CO3 solution (46 mL, 46.0 mmol) added and the mixture heated to 80° C. for 20 h. The reaction mixture was filtered, partially evaporated and EtOAc (200 mL) and 1 N HCl (100 mL) added. The organic layer washed with 1N HCl and saturated sodium bicarbonate, dried over sodium sulfate, and evaporated. The crude material was filtered through a silica plug (THF) to give 3′-chloro-4′-fluoro-4-hydroxy-biphenyl-3-carboxylic acid (2.15 g).

後処理

  1. filtrationThe reaction mixture was filtered
  2. custompartially evaporated
  3. additionEtOAc (200 mL) and 1 N HCl (100 mL) added
  4. washThe organic layer washed with 1N HCl and saturated sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. filtrationThe crude material was filtered through a silica plug (THF)

出典と根拠

ORDレコード
ord-90c5c581e3844ef390a161f7f73dad68
出典データセット
uspto-grants-2008_12
特許番号
US07459472B2

反応ノート

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