Hydrochloric Acid → 2-Amino-5-bromo[1,1'-biphenyl]-3-sulphonic acid

HRID 727436노트

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HRID 727436 반응식
[NH2:1][C:2]1[C:7](I)=[CH:6][C:5]([Br:9])=[CH:4][C:3]=1[S:10]([OH:13])(=[O:12])=[O:11].C(=O)([O-])[O-].[Na+].[Na+].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.S(=O)(=O)(O)O>COCCOC.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.CO>[NH2:1][C:2]1[C:3]([S:10]([OH:13])(=[O:12])=[O:11])=[CH:4][C:5]([Br:9])=[CH:6][C:7]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 189193852-Amino-5-bromo-3-iodobenzenesulphonic acid

생성물 1

HCID 189316672-Amino-5-bromo[1,1'-biphenyl]-3-sulphonic acid

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
0 °C

실험 절차

To a mixture of 37.8 g (100 mmol) of 2-amino-5-bromo-3-iodobenzenesulphonic acid and 32 g (300 mmol) of sodium carbonate in 300 ml of 1,2-dimethoxyethane and 150 ml of water are successively added, under a nitrogen atmosphere, 5.8 g (5 mmol) of tetrakis(triphenylphosphine)palladium (0) and 19.5 g (160 mmol) of benzeneboronic acid. The mixture is heated at the reflux temperature for 4 hours and the reaction medium is then concentrated under reduced pressure. The residue thus obtained is then dissolved in a mixture containing 300 ml of methanol, 300 ml of 0.1N hydrochloric acid and 16 ml of 95% sulphuric acid. The mixture is concentrated to 100 ml under reduced pressure, cooled to 0° C. and filtered. The residue is purified by chromatography on an RP 18 reverse-phase column, eluting with an acetonitrile:water mixture (2:8).

후처리

  1. additionare successively added, under a nitrogen atmosphere
  2. temperatureThe mixture is heated at the reflux temperature for 4 hours
  3. concentrationthe reaction medium is then concentrated under reduced pressure
  4. customThe residue thus obtained
  5. dissolutionis then dissolved in a mixture
  6. concentrationThe mixture is concentrated to 100 ml under reduced pressure
  7. filtrationfiltered
  8. customThe residue is purified by chromatography on an RP 18 reverse-phase column
  9. washeluting with an acetonitrile

출처 및 근거

ORD 기록
ord-9d0f647a178945ec88aa837ce90d1f64
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712393

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