Hydrochloric Acid → 2-Fluoro-3-(3-fluorophenyl)-5-methyl-benzoic acid

HRID 1771617ノート

反応式

HRID 1771617 の反応式
Br[C:2]1[C:3]([F:12])=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[C:5]([OH:7])=[O:6].[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+].Cl>C(#N)C.O.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>[F:12][C:3]1[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)=[CH:10][C:9]([CH3:11])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 125134713-Bromo-2-fluoro-5-methylbenzoic acid

生成物 1

HCID 894435072-Fluoro-3-(3-fluorophenyl)-5-methyl-benzoic acid収率 75%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 3-bromo-2-fluoro-5-methyl-benzoic acid (400 mg, 1.7 mmol, 1.0 eq), (3-fluorophenyl)boronic acid (720 mg, 5.2 mmol, 3.0 eq), K2CO3 (356 mg, 2.6 mmol, 1.5 eq) and Pd(PPh3)4 (396.0 mg, 0.40 mmol, 0.2 eq) in acetonitrile (5 mL) and H2O (4 mL) was heated at reflux overnight. The reaction was acidified to pH 3 by addition of 1M HCl and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title compound as a solid (160 mg, 75%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:4)

出典と根拠

ORDレコード
ord-19e6800bfa664814815290fed911bfe5
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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