N-bromobutanimide → HCID 86761592, compound

HRID 1517550Notes

Reaction equation

HRID 1517550 reaction equation
[Br:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([OH:11])=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl.O>[Br:23][C:6]1[C:5]([OH:11])=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=[C:2]([Br:1])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86761593HCID 86761593, compound

Product 1

HCID 86761592HCID 86761592, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

step 3—To a solution of 120 (1.0 eq, 2.27 mmol, 621 mg) in DCM (10 mL) at RT was added in three portions NBS (2.0 eq, 4.55, 809 mg). The mixture was stirred RT for 30 min. The reaction was diluted with water, the organic layer was separated, dried (MgSO4) and concentrated to afford 767 mg of 2,6-dibromo-4-tert-butyl-3-hydroxybenzoic acid (122) as a light brownish solid.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-de16c824b4a549d9b52b1b5caeb61a5e
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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