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tert-Butanol → Tert-butyl 2-(3-bromophenyl)acetate

HRID 1595915
ノート
印刷プレビュー

反応式

HRID 1595915 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:12](O)([CH3:15])([CH3:14])[CH3:13].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:12]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:15])([CH3:14])[CH3:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 74653(3-Bromophenyl)acetic acid

生成物 1

HCID 53936336Tert-butyl 2-(3-bromophenyl)acetate収率 89.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane
溶媒

実験手順

A mixture of 3-bromophenyl acetic acid (5.00 g, 23.24 mmol), tert-butanol (1.89 g, 25.57 mmol), DMAP (3.12 g, 25.57 mmol), and DCC (5.27 g, 25.57 mmol) in CH2Cl2 (150 mL) was stirred for 24 h at room temperature. The reaction was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc and the mixture was filtered. The organic solution was washed consecutively with 5.5% HCl, water, saturated NaHCO3, and brine. The organic solution was dried over MgSO4, filtered, and concentrated to provide the title compound (5.64 g).

後処理

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. filtrationthe mixture was filtered
  5. washThe organic solution was washed consecutively with 5.5% HCl, water, saturated NaHCO3, and brine
  6. dry with materialThe organic solution was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c5e2e31165cb4e59bcfe01d243231881
出典データセット
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06288120B1

反応ノート

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