Hexane → HCID 19841466, compound

HRID 1638752Notes

Reaction equation

HRID 1638752 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1[OH:12].[Br:13]N1C(=O)CCC1=O.CCCCCC.C(OCC)(=O)C>C(Cl)Cl>[Br:13][C:4]1[C:5]([CH3:11])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([CH3:1])[C:3]=1[OH:12]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 2821102,5-Dimethyl-4-nitrophenol

Product 1

HCID 19841466HCID 19841466, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a magnetically stirred suspension of 2,5-dimethyl-4-nitrophenol (12.70 grams, 75.98 mmol) in CH2Cl2 (150 milliliters) at room temperature was added portionwise N-bromosuccinimide (14.88 grams, 83.58 mmol). The mixture rapidly became homogeneous and after one hour thin layer chromatography (3:1 hexane:ethyl acetate) indicated complete consumption of the starting material and formation of a single major product. Saturated Na2SO3 solution (15 milliliters) was added and the solvent was removed under reduced pressure. Ethyl acetate was then added and the organic layer was washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure to afford 2-bromo-3,6-dimethyl-4-nitrophenol (13.6 grams, 55.3 mmol, 73%) as a rust colored solid. H'-NMR (CDCl3) 9.26 (brS, 1H), 7.71 (S, 1H), 2.60 (S, 3H), 2.31 (S, 3H).

Workup

  1. customconsumption of the starting material and formation of a single major product
  2. additionSaturated Na2SO3 solution (15 milliliters) was added
  3. customthe solvent was removed under reduced pressure
  4. additionEthyl acetate was then added
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77f6222ffad14e63bff410de596caff8
Source dataset
uspto-grants-1989_11
Patent number
US04880838

Reaction notes

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