Hydrochloric Acid → (4-Chloro-3-methoxyphenyl)boronic acid

HRID 70556

反応式

HRID 70556 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([Cl:15])[CH:8]=1.[B:16](OC)([O:19]C)[O:17]C.Cl>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[Cl:15][C:9]1[CH:8]=[CH:7][C:12]([B:16]([OH:19])[OH:17])=[CH:11][C:10]=1[O:13][CH3:14]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 30165374-Bromo-2-chloroanisoleHCID 178418339Butyllithium

生成物 1

HCID 23005377(4-Chloro-3-methoxyphenyl)boronic acid

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

n-Butyllithium (2.76 M, 2.5 mL) was added dropwise to a solution of commercially available 4-bromo-2-chloroanisole (1.0 g) in toluene (8 mL) and tetrahydrofuran (3 mL) at −78° C., and the mixture was stirred as such for 30 minutes. Thereafter, trimethyl borate (1.0 mL) was added and the mixture was stirred at room temperature for 15 minutes. Dilute hydrochloric acid and ethyl acetate were added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→98:2) to give the title compound as a colorless powder (535 mg).

後処理

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→98:2)

出典と根拠

ORDレコード
ord-127ee59c2c744610a05c65fd6f46695a
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

関連ノート

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