N-bromobutanimide → HCID 66643855、化合物

HRID 1186944ノート

反応式

HRID 1186944 の反応式
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].C1C(=O)N([Br:18])C(=O)C1>C(O)(C(F)(F)F)=O>[Br:18][C:6]1[CH:5]=[CH:4][C:3]([OH:10])=[C:2]([Cl:1])[C:7]=1[CH2:8][OH:9]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 155506102-Chloro-3-(hydroxymethyl)phenol

生成物 1

HCID 66643855HCID 66643855、化合物

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To the flask charged with 2-chloro-3-(hydroxymethyl)phenol from Step A and a stir bar was added NBS (10.8 g, 60.5 mmol) and TFA (50 mL). The reaction was allowed to stir for 16 hours at RT. TLC showed complete reaction at that point. The solvent was removed under vacuum. The residue was re-dissolved in EtOAc, washed with water, and purified by silica gel flash chromatography. A pair of regio-isomers was collected from the separation. The less polar spot was the desired 4-bromo-2-chloro-3-(hydroxymethyl)phenol according to noe NMR analysis. 1H-NMR (500 MHz, CDCl3) δ ppm 7.42 (d, J=8.5 Hz, 1H), 6.92 (d, J=8.5 Hz, 1H), 4.96 (s, 2H).

後処理

  1. customreaction at that point
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was re-dissolved in EtOAc
  4. washwashed with water
  5. custompurified by silica gel flash chromatography
  6. customA pair of regio-isomers was collected from the separation

出典と根拠

ORDレコード
ord-a270cf6d11a441c0af3191d7904bb8c1
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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