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Water → Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

HRID 495176
Notes
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Reaction equation

HRID 495176 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.[Br:20]N1C(=O)CCC1=O.O>CN(C)C=O>[CH3:14][O:13][CH2:12][O:11][C:9]1[C:8]([Br:20])=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:6]=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 23116398Methyl 3,5-bis(methoxymethoxy)phenylacetate

Product 1

HCID 68420121Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

Methyl 3,5-bis(methoxymethoxy)phenylacetate (43 g, 0.16 mol) obtained in Example 1, Step 1 was dissolved in N,N-dimethylformamide (0.68 L). After the solution was cooled to 4° C., N-bromosuccinimide (28 g, 0.16 mol) was added thereto, followed by stirring for 3 hours, while the temperature of the reaction mixture was raised to room temperature. To the reaction mixture was added water (0.50 L), and the mixture was extracted with a mixed solvent of hexane and ethyl acetate (hexane/ethyl acetate=1/2, 0.40 L×4). The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL) and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/2) to obtain a quantitative yield of methyl 3,5-bis(methoxymethoxy)-2-bromophenyl-acetate.

Workup

  1. temperaturewas raised to room temperature
  2. extractionthe mixture was extracted with a mixed solvent of hexane and ethyl acetate (hexane/ethyl acetate=1/2, 0.40 L×4)
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/2)

Sources & evidence

ORD record
ord-fd841cbea225467c8ba294a186da3e15
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538224B2

Reaction notes

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