Water → 3,5-Bis(methoxymethoxy)-2-bromo-1-(2-methoxyethyl)benzene

HRID 495174Notes

Reaction equation

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

Participants

Conditions

Temperature: 4 °C

Procedure

1,3-Bis(methoxymethoxy)-5-(2-methoxyethyl)benzene (5.00 g, 19.5 mmol) obtained in Example 1, Step 3 was dissolved in N,N-dimethylformamide (40 mL). After the solution was cooled to 4° C., N-bromosuccinimide (3.47 g, 19.5 mmol) was added thereto, followed by stirring for 1 hour. To the reaction mixture was added water (0.10 L), and the mixture was extracted with a mixed solvent of hexane and ethyl acetate (hexane/ethyl acetate=1/1, 0.30 L). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2) to obtain 3,5-bis(methoxymethoxy)-2-bromo-1-(2-methoxyethyl)benzene (5.7 g, 87%).

Workup

extractionthe mixture was extracted with a mixed solvent of hexane and ethyl acetate (hexane/ethyl acetate=1/1, 0.30 L)
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-1/2)

Sources & evidence

ORD record: ord-9c699ea4761549e59e4855e6f1e83baa
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538224B2

Reaction notes

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