N-bromobutanimide → (2-Bromo-4-tert-butyl-5-methoxy-phenyl)-methanol

HRID 2390861Notes

Reaction equation

HRID 2390861 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][C:6]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl.OS([O-])=O.[Na+]>[Br:22][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([O:13][CH3:14])=[CH:7][C:8]=1[CH2:11][OH:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 534014571206775-43-0

Product 1

HCID 67070042(2-Bromo-4-tert-butyl-5-methoxy-phenyl)-methanolYield 100%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 23665763Sodium BisulfiteSolvent

Procedure

step b—To a solution of 345 (2.08 g, 10.70 mmol) in CCl4 (75 mL) was added NBS (2.10 g, 11.80 mmol). The reaction was stirred for 15 min then diluted with a cold 10% aqueous NaHSO3. The reaction mixture was extracted with DCM. The organic extract was washed with brine, dried (MgSO4), filtered and concentrated. The residue was taken up in hexanes (80 mL) and then concentrated to afford 2.9 g (100%) of 344a as a white solid.

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e744d1e0f6d4be5a7ac2ddaf8c8ce87
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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