Hydrochloric Acid → 6,7-Difluoro-5-(2-methoxyethoxymethoxy)-2-methylbenzofuran-4-carbaldehyde

HRID 2244847Notes

Reaction equation

Br[C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([F:12])=[C:4]([F:13])[C:3]=1[O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20].[Li]CCCC.[CH:26](N1CCOCC1)=[O:27].Cl>C1COCC1>[F:13][C:4]1[C:5]([F:12])=[C:6]2[O:10][C:9]([CH3:11])=[CH:8][C:7]2=[C:2]([CH:26]=[O:27])[C:3]=1[O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20]

Participants

Conditions

Temperature: -10 °C

Procedure

27.2 g (77.5 mmol) of 4-bromo-6,7-difluoro-5-(2-methoxyethoxymethoxy)-2-methylbenzofuran are initially introduced at −75° C. in 500 ml of THF, and 52.0 ml (85.2 mmol) of n-BuLi (15% soln. in hexane) are added. After 2 h at this temperature, 15.5 ml (155 mmol) of N-formylmorpholine are metered in, and the batch is stirred at this temperature for 2 h. The reaction soln. is slowly warmed to −10° C. and hydrolysed using dil. HCl. The batch is extracted with MTBE, and the combined organic phases are washed with sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:MTBE=2:1→n-heptane:MTBE=1:1).

Workup

extractionThe batch is extracted with MTBE
washthe combined organic phases are washed with sat. sodium chloride soln
customThe solution is dried
concentrationconcentrated to dryness
customThe residue is purified by column chromatography (SiO2, n-heptane:MTBE=2:1→n-heptane:MTBE=1:1)

Sources & evidence

ORD record: ord-d107c20b3b2447ebb547a10cd5c83b43
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678929B2

Reaction notes

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