1,4-Dibromobutane → HCID 11045330, compound

HRID 404985Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9][CH2:10][CH2:11]Br.[OH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25]>CC#N>[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][O:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (0.758 g, 0.48 mmol) was added to a solution of 1,4-dibromo butane (1.18 g, 5.49 mmol) and methyl 4-hydroxy-3-methoxybenzoate (0.5 g, 2.74 mmol) in CH3CN (10 mL). After stirring for 12 h at 80° C., the organic phase was evaporated under reduced pressure and the crude material was partitioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (3×20 mL). The organic phase was dried using Na2SO4 and evaporated to give the crude methyl 4-(4-bromobutoxy)-3-methoxybenzoate which was purified by column chromatography using hexanes:ethyl acetate to give the pure product as a colorless solid (0.692 g, 80%). 1H NMR (400 MHz, CDCl3): δ 7.61 (d, 1H, J=8.3 Hz), 7.51 (s, 1H), 6.83 (d, 1H, J=8.2 Hz), 4.07 (t, 2H, J=5.7 Hz), 3.87 (s, 3H), 3.85 (s, 3H), 3.47 (t, 2H, J=6.4 Hz), 2.04-2.00 (m, 4H). LC-MS (ESI) Calcd for C13H17BrO4 [M+H]+: 317.03, 319.03. Found: 316.90, 318.90.

Workup

customthe organic phase was evaporated under reduced pressure
customthe crude material was partitioned between water and CH2Cl2
extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
customThe organic phase was dried
customevaporated
customto give the crude methyl 4-(4-bromobutoxy)-3-methoxybenzoate which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-ede0815865f74508a101689e310e5b3a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748632B2

Reaction notes

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