Butyl bromide → Butyl 4-bromo-3-(butyloxy)benzoate

HRID 2098893ノート

反応式

HRID 2098893 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:19][CH2:20][CH2:21][CH3:22])=[O:7])=[CH:4][C:3]=1[O:11][CH2:10][CH2:2][CH2:3][CH3:4]

参加物

6

反応物 3

HCID 8002Butyl bromideHCID 10796Cesium carbonateHCID 64209734-Bromo-3-hydroxybenzoic acid

生成物 1

HCID 57467609Butyl 4-bromo-3-(butyloxy)benzoate収率 66.81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a flask containing 4-bromo-3-hydroxybenzoic acid (D.1) (available from Combi-Blocks Inc.) (2.40 g, 11.06 mmol) and cesium carbonate (8.287 g, 25.44 mmol) in DMF (40 mL), was added 1-bromobutane (2.494 mL, 23.22 mmol), and the mixture was stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by CombiFlash® chromatography (0 to 20% EtOAc/hexanes) to provide D.2 (2.4326 g, 66.81% yield).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by CombiFlash® chromatography (0 to 20% EtOAc/hexanes)
  7. customto provide D.2 (2.4326 g, 66.81% yield)

出典と根拠

ORDレコード
ord-68808c05ec394b43bcee50df20da8fa2
出典データセット
uspto-grants-2013_05
特許番号
US08450522B2

反応ノート

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