1,3-Dibromo-5,5-dimethylhydantoin → Methyl 3-bromo-2-hydroxy-6-methylbenzoate

HRID 1778368Notes

Reaction equation

HRID 1778368 reaction equation
[Br:1]N1C(C)(C)C(=O)N(Br)C1=O.[CH3:12][CH:13]1[CH:18]([C:19]([O:21][CH3:22])=[O:20])[C:17](=[O:23])[CH:16]=[CH:15][CH2:14]1.C(NC(C)C)(C)C>C(Cl)Cl>[Br:1][C:16]1[C:17]([OH:23])=[C:18]([C:13]([CH3:12])=[CH:14][CH:15]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoin2×HCID 7912DiisopropylamineHCID 15581456Methyl 6-methyl-2-oxocyclohex-3-ene-1-carboxylate

Product 1

HCID 66685369Methyl 3-bromo-2-hydroxy-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,3-dibromo-5,5-dimethylhydantoin (65 g) in DCM (150 mL) was added dropwise to a stirred and cooled solution of methyl 6-methyl-2-oxocyclohex-3-enecarboxylate (prepared in a similar manner to Hauser et al, Synthesis 1980 814, 75.16 g) and N,N-di-isopropylamine (6.15 mL) in DCM (500 mL) at 0° C. and the resultant mixture was stirred at room temperature for 3 days. The mixture was recooled to 0° C. and further 1,3-dibromo-5,5-dimethylhydantoin (11 g) was added and the mixture was stirred at 0° C. for 3 hours. The precipitate was removed by filtration and the filtrate was evaporated to dryness to give methyl 3-bromo-2-hydroxy-6-methylbenzoate (114.5 g) as an oil.

Workup

  1. customwas recooled to 0° C.
  2. stirringthe mixture was stirred at 0° C. for 3 hours
  3. customThe precipitate was removed by filtration
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-d4bc64f8061b4fc1a4a538245d26deb5
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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