Sodium Hydroxide → HCID 68154114, compound

HRID 1183246Notes

Reaction equation

[Br-].[N+:2]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[F:31][C:32]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:33]=1[CH:34]=O.[OH-].[Na+]>C(Cl)Cl>[F:31][C:32]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:33]=1/[CH:34]=[CH:9]/[C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 956 mg (2 mmol) of (4-nitrobenzyl)triphenylphosphonium bromide and 284 mg (2 mmol) of 2,6-difluorobenzaldehyde in 20 mL of CH2Cl2 was added 5 mL of 0.48 M NaOH solution (2.4 mmol, 1.2 equiv) dropwise over a 10 min period. The red solution was heated at 50° C. for 1 h. The organic layer was separated, washed with a saturated aqueous NaHSO3 solution and water, and dried over anhydrous MgSO4. The residue was recrystallized from ethanol to afford 360 mg (69%) of 8 as light yellow crystals: mp 136-137° C. 1H NMR (DMSO-d6): δ 8.23 (d, 2H, J=8.8 Hz), 7.93 (d, 2H, J=8.8 Hz), 7.50 (d, 1H, J=16.8 Hz), 7.46-7.40 (m, 1H), 7.37 (d, 1H, J=16.8 Hz), 7.23-7.17 (m, 2H). 13C NMR (DMSO-d6): δ 160.79 (dd, J1=249.4 Hz, J2=7.3 Hz, two C), 147.27, 143.81, 133.35 (t, J=7.9 Hz), 130.82 (t, J=10.7 Hz), 128.21 (two C), 124.46 (two C), 119.70 (t, J=1.6 Hz), 113.79 (t, J=15.1 Hz), 112.65 (dd, J1=19.5 Hz, J2=5.9 Hz, two C). MS: m/z (%) 261 (61), 231 (67), 214 (45), 194 (34), 183 (100). Anal. Calcd for C14H9F2NO: C, 64.37; H, 3.47. Found: C, 64.56; H, 3.42.

Workup

customThe organic layer was separated
washwashed with a saturated aqueous NaHSO3 solution and water
dry with materialdried over anhydrous MgSO4
customThe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-a5422f0cc19649e690bcbb83bb600fcb
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664276B2

Reaction notes

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