N-bromobutanimide → HCID 66643855, compound

HRID 1501832Notes

Reaction equation

HRID 1501832 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 66643855HCID 66643855, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a flask charged with 2-chloro-3-(hydroxymethyl)phenol 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, then 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 NMR analysis.

Workup

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

Sources & evidence

ORD record
ord-0249c917f09b4603ad2d4452e8fa58c5
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

Loading…