N-bromobutanimide → HCID 66643855, 화합물

HRID 1186944노트

반응식

HRID 1186944 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 66643855HCID 66643855, 화합물

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a270cf6d11a441c0af3191d7904bb8c1
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673920B2

반응 노트

불러오는 중…