Water → 2-(Benzyloxymethyl)-3-bromo-4,6-bis(methoxymethoxy)benzoic acid

HRID 505653Notes

Reaction equation

HRID 505653 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH:18]=[C:17]([O:19][CH2:20][O:21][CH3:22])[CH:16]=[C:15]([O:23][CH2:24][O:25][CH3:26])[C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:27]N1C(=O)CCC1=O.O>CN(C)C=O>[CH2:1]([O:8][CH2:9][C:10]1[C:18]([Br:27])=[C:17]([O:19][CH2:20][O:21][CH3:22])[CH:16]=[C:15]([O:23][CH2:24][O:25][CH3:26])[C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 687174092-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid

Product 1

HCID 866163832-(Benzyloxymethyl)-3-bromo-4,6-bis(methoxymethoxy)benzoic acidYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid (60 mg, 0.17 mmol) obtained in Step 6 of Example 22 was dissolved in N,N-dimethylformamide (10 mL), and N-bromosuccinimide (62 mg, 0.35 mmol) was added thereto followed by stirring at a room temperature for 2 hours. The reaction mixture was added with water and extracted with chloroform 3 times. The organic layers were combined and sequentially washed with saturated aqueous sodium thiosulfate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1) to obtain 2-(benzyloxymethyl)-3-bromo-4,6-bis(methoxymethoxy)benzoic acid (16 mg, 22%).

Workup

  1. extractionextracted with chloroform 3 times
  2. washsequentially washed with saturated aqueous sodium thiosulfate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-2d5e4cc771df4346a6df611b0ac701ec
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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