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Sodium Carbonate → 2-(2-Chloro-2',6'-difluoro-4'-methoxybiphenyl-4-yl)acetic acid

HRID 1930107
ノート
印刷プレビュー

反応式

HRID 1930107 の反応式
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[F:11].[Cl:12][C:13]1[CH:18]=[C:17]([CH2:19][C:20]([O:22]C)=[O:21])[CH:16]=[CH:15][C:14]=1B(O)O.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:12][C:13]1[CH:18]=[C:17]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:15][C:14]=1[C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[F:11]
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

6

反応物 3

HCID 10340Sodium CarbonateHCID 27249844-Bromo-3,5-difluoroanisoleHCID 59627663(2-Chloro-4-(2-methoxy-2-oxoethyl)phenyl)boronic acid2 回

生成物 1

HCID 596277152-(2-Chloro-2',6'-difluoro-4'-methoxybiphenyl-4-yl)acetic acid収率 72.4%

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
85 °C

実験手順

A solution of 4-bromo-3,5-difluoroanisole (645 mg, 2.89 mmol) and 2-chloro-4-(2-methoxy-2-oxoethyl)phenylboronic acid (Intermediate 2-6; 859 mg, 3.76 mmol) and sodium carbonate (2.89 mL, 5.78 mmol), tetrakis(triphenylphosphine)palladium(0) (207 mg, 0.18 mmol) in DME (20 mL) was degassed and then stirred at 85° C. for 17 hours. The reaction mixture was allowed to cool, evaporated and partitioned between EtOAc (75 mL), water (40 mL) and saturated brine (15 mL), The aqueous phase was acidified with 2M HCl and extracted into EtOAc (2×125 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford 2-(2-chloro-2′,6′-difluoro-4′-methoxybiphenyl-4-yl)acetic acid (654 mg, 72.4%) as a white solid, which was used without further purification.

後処理

  1. temperatureto cool
  2. customevaporated
  3. custompartitioned between EtOAc (75 mL), water (40 mL) and saturated brine (15 mL)
  4. extractionextracted into EtOAc (2×125 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-4811505286454c2d8e25c9b85377ff83
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188092B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート