Triethylamine → 1-[2-(4-Bromo-2-chloromethylphenoxy)ethyl]pyrrolidine

HRID 734847

反応式

HRID 734847 の反応式
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([O:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:10]([CH2:12]O)[CH:11]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([O:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:10]([CH2:12][Cl:3])[CH:11]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 211828631-[2-(2-Hydroxymethyl-4-bromophenoxy)ethyl]pyrrolidine

生成物 1

HCID 690598221-[2-(4-Bromo-2-chloromethylphenoxy)ethyl]pyrrolidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.16 mL (2.20 mmol) of thionyl chloride was added at −10° C. to a solution of 0.60 g (2.00 mmol) of [5-bromo-2-(2-pyrrolidin-1-ylethoxy)phenyl]methanol and 0.42 mL (3.00 mmol) of triethylamine in 30 mL of THF and the mixture was stirred for 16 hours at RT. Ice and dilute aqueous sodium bicarbonate solution was added to the reaction mixture and the phases were separated. The aqueous phase was exhaustively extracted with DCM, and the combined organic phases were washed with water, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 0.39 g (62% of theoretical); C13H17BrClNO (M=318.637); calc.: molpeak (M+H)+: 318/320/322 (BrCl); found: molpeak (M+H)+: 318/320/322 (BrCl); HPLC-MS: 5.84 minutes (method A).

後処理

  1. customthe phases were separated
  2. extractionThe aqueous phase was exhaustively extracted with DCM
  3. washthe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down in vacuo
  6. custom5.84 minutes (method A)

出典と根拠

ORDレコード
ord-59de8ca491d041b88695725a4313be7d
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

関連ノート

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