Water → Dimethyl 5-bromo-4-hydroxybenzene-1,3-dicarboxylate

HRID 423265Notes

Reaction equation

HRID 423265 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[Br:16]N1C(=O)CCC1=O.O.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([Br:16])[C:11]([OH:14])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 80087Dimethyl 4-hydroxyisophthalateHCID 516892Sodium Bicarbonate

Product 1

HCID 58629779Dimethyl 5-bromo-4-hydroxybenzene-1,3-dicarboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxyisophthalic acid dimethyl ester (10.51 g) in THF (100 mL) was added N-bromosuccinimide (9.34 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Water (200 mL) and saturated aqueous sodium bicarbonate (100 mL) were successively added to the reaction solution. The resulting precipitate was filtered, washed successively with saturated aqueous sodium bicarbonate and water, and dried to give the title compound (12.5 g).

Workup

  1. temperaturecooling
  2. filtrationThe resulting precipitate was filtered
  3. washwashed successively with saturated aqueous sodium bicarbonate and water
  4. customdried

Sources & evidence

ORD record
ord-a23bf3d8051f472ca041643a58a73966
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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