Calcium Carbonate → HCID 86605682, 화합물

HRID 860964노트

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HRID 860964 반응식
[Br-:1].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([O-])([O-])=O.[Ca+2].[Cl:42][C:43]1[C:44]([CH3:64])=[C:45]([CH:49]=[C:50]([Cl:63])[C:51]=1[O:52][C:53]1[CH:58]=[CH:57][C:56]([OH:59])=[C:55]([CH:60]([CH3:62])[CH3:61])[CH:54]=1)[C:46]([OH:48])=[O:47]>CO.C(Cl)Cl>[Cl:42][C:43]1[C:44]([CH3:64])=[C:45]([CH:49]=[C:50]([Cl:63])[C:51]=1[O:52][C:53]1[CH:54]=[C:55]([CH:60]([CH3:61])[CH3:62])[C:56]([OH:59])=[C:57]([Br:1])[CH:58]=1)[C:46]([OH:48])=[O:47]

참가 물질

5

반응물 3

HCID 10112Calcium CarbonateHCID 21339097HCID 21339097, 화합물HCID 53442637Benzyltrimethylammoniumtribromide

생성물 1

HCID 86605682HCID 86605682, 화합물수율 32.7%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

A suspension of benzyltrimethylamonium tribromide (2.2 g, 5.63 mmol) and CaCO3 (0.28 g, 2.82 mmol) was stirred for 2 hr at 20° C. in a 1:1 MeOH/CH2Cl2 solution (10 mL) containing 3,5-dichloro-2-methyl-4-(4-hydroxy-3-isopropylphenoxy)-benzoic acid (1.0 g, 2.82 mmol). Once HPLC analysis indicated that conversion to the desired monobrominated phenol was optimal, the reaction was quenched by addition of 15 mL of 1N HCl. After removal of the organic solvents under vacuum using a rotary evaporator, the aqueous suspension was extracted twice with EtOAc. After drying the combined EtOAc layers over MgSO4, the salts were filtered prior to removal of the EtOAc under vacuum. The resulting residue after purification by gradient elution from a reverse phase C18 column employing MeOH/H2O containing 0.1% TFA yielded 3,5-dichloro-2-methyl-4-(3-bromo-4-hydroxy-5-isopropylphenoxy)benzoic acid (400 mg).

후처리

  1. customthe reaction was quenched by addition of 15 mL of 1N HCl
  2. customAfter removal of the organic solvents under vacuum
  3. customa rotary evaporator
  4. extractionthe aqueous suspension was extracted twice with EtOAc
  5. dry with materialAfter drying the combined EtOAc layers over MgSO4
  6. filtrationthe salts were filtered
  7. customto removal of the EtOAc under vacuum
  8. customThe resulting residue after purification
  9. washby gradient elution from a reverse phase C18 column

출처 및 근거

ORD 기록
ord-f2c5fe9231f34969b5e0a285847f479d
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153997B2

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