Calcium Carbonate → HCID 86605682、化合物

HRID 860964ノート

反応式

HRID 860964 の反応式
[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]

参加物

5

反応物 3

HCID 10112Calcium CarbonateHCID 21339097HCID 21339097、化合物HCID 53442637Benzyltrimethylammoniumtribromide

生成物 1

HCID 86605682HCID 86605682、化合物収率 32.7%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f2c5fe9231f34969b5e0a285847f479d
出典データセット
uspto-grants-2006_12
特許番号
US07153997B2

反応ノート

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