N-bromobutanimide → HCID 66643855, compound

HRID 1186944Notes

Reaction equation

HRID 1186944 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 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).

Workup

  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

Sources & evidence

ORD record
ord-a270cf6d11a441c0af3191d7904bb8c1
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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