Ammonium Chloride → HCID 58884965, compound

HRID 910164Notes

Reaction equation

[CH:1]([N:4]([CH:14]([CH3:16])[CH3:15])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=1)([CH3:3])[CH3:2].[Li]CCCC.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][C:24]=1[O:31][CH3:32].[NH4+].[Cl-]>C1COCC1>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]([OH:28])[C:9]2[CH:10]=[CH:11][C:6]([C:5]([N:4]([CH:14]([CH3:16])[CH3:15])[CH:1]([CH3:3])[CH3:2])=[O:13])=[CH:7][CH:8]=2)=[CH:25][C:24]=1[O:31][CH3:32]

Participants

Conditions

Temperature: -78 °C

Procedure

N,N-Diisopropyl-4-iodobenzamide (6.0 g, 18 mmol) was dissolved in THF (200 mL) and cooled to −78° C. under nitrogen atmosphere. n-BuLi (14 mL, 1.3 M solution in hexane, 18 mmol) was added dropwise during 10 min at −65 to −78° C. 4-fluoro-3-methoxybenzaldehyde (2.8 g, 18 mmol) was added dropwise dissolved in THF (5 mL). NH4Cl (aq.) was added after 30 min. After concentration in vacuo, extraction with EtOAc/water, drying (MgSO4) and evaporation of the organic phase, the residue was purified by chromatography on silica (0-75% EtOAc/heptane) to yield the desired product (3.9 g, 60%). 1H NMR (CDCl3) δ 1.0-1.6 (m, 12H), 2.65 (d, J=4 Hz, 1H), 3.4-3.9 (m, 2H), 3.80 (s, 3H), 6.10 (d, J=4 Hz, 1H), 6.76 (m, 1H), 6.95 (m, 1H), 7.04 (m, 1H), 6.76 (m, 1H), 7.25, 7.40 (2d, J=7.5 Hz, 4H).

Workup

concentrationAfter concentration
extractionin vacuo, extraction with EtOAc/water
customdrying
custom(MgSO4) and evaporation of the organic phase
customthe residue was purified by chromatography on silica (0-75% EtOAc/heptane)

Sources & evidence

ORD record: ord-af9ad729e7cc4b1a817d2399284fa3ff
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022074B2

Reaction notes

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