N-bromobutanimide → HCID 66643855, compound

HRID 1848519Notes

Reaction equation

HRID 1848519 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-96d905f98d724644992baf1f4f2bf272
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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