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Hydrochloric Acid → 2'-Chloro-2-chloro-5-methoxy-[1,1'-biphenyl]-4-carboxylic acid

HRID 1830060
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HRID 1830060 반응식
I[C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:11][C:10]1[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]([O:12][CH3:13])=[CH:3][C:2]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14]
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 167918585-Chloro-4-iodo-2-methoxybenzoic acid

생성물 1

HCID 219477112'-Chloro-2-chloro-5-methoxy-[1,1'-biphenyl]-4-carboxylic acid수율 74.8%

시약·촉매·용매 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 4-iodo-5-chloro-2-methoxy benzoic acid of Example 5, Step A (3.38 g, 10.8 mmol) in N,N-dimethylformamide (80 mL) was added 2-chloro phenyl boronic acid (5.07 g, 32.4 mmol) and potassium carbonate (3.44 g, 32.4 mmol). This mixture was purged with nitrogen and then treated with tetrakis(triphenylphosphine) palladium(0) (0.625 g, 0.54 mmol). The reaction was heated to reflux overnight, cooled, acidified with 2 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to provide 2.4 g of the title acid which was used in the next step without further purification.

후처리

  1. customThis mixture was purged with nitrogen
  2. temperatureThe reaction was heated
  3. temperatureto reflux overnight
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

출처 및 근거

ORD 기록
ord-2b0fd1a23224442481cd138c871a7f2f
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07064120B2

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