4-Butoxybenzaldehyde → HCID 86600085, compound

HRID 2373143Notes

Reaction equation

HRID 2373143 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[Br:14][C:15]1[CH:20]=[C:19]([CH2:21]P(OCC)(=O)OCC)[C:18]([Br:30])=[CH:17][C:16]=1[CH2:31]P(OCC)(=O)OCC.[CH3:40][C:41]([O-:44])(C)[CH3:42].[K+]>C1COCC1>[Br:30][C:18]1[CH:17]=[C:16](/[CH:31]=[CH:10]/[C:9]2[CH:12]=[CH:13][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=2)[C:15]([Br:14])=[CH:20][C:19]=1/[CH:21]=[CH:12]/[C:9]1[CH:10]=[CH:42][C:41]([O:44][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:40][CH:8]=1

Participants

5

Reactant 3

HCID 798134-ButoxybenzaldehydeHCID 23665647Potassium tert-butoxideHCID 58019391P,P,P′,P′-Tetraethyl P,P′-[(2,5-dibromo-1,4-phenylene)bis(methylene)]bis[phosphonate]

Product 1

HCID 86600085HCID 86600085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of p-butoxybenzaldehyde (71) (0.7 g, 3.95 mmol) and tetraethyl 2,5-dibromo-α,α′-p-xylenebisphosphonate (69) (1.02 g, 1.90 mmol) in dry THF (25 ml) at 0° C. was added 4 ml of 1 M solution of KOtBu in THF. After 2 hours the reaction was quenched by addition of 20 ml of methanol. A yellow solid was collected by filtration and washed three times with methanol to afford NMR-pure product in 0.92 g (82.9%) yield.1H NMR (CDCl3, 500 MHz) δppm: 7.83 (s, 2H), 7.48 (d, J=8.5 Hz, 4H), 7.22 (d, J=16.5 Hz, 2H, ═CH), 7.01 (d, J=16.0 Hz, 2H, ═CH), 6.91 (d, J=9.0 Hz, 4H), 4.0 (t, J=6.5 Hz, 4H, CH2), 1.80 (m, 4H, CH2), 1.52 (m, 4H, CH2), 0.99 (t, J=7.2 Hz, 6H, CH3)—C NMR (CDCl3, 125.7 MHz) δppm: 159.5, 137.2, 131.6, 129.9, 129.2, 128.2, 123.4, 122.8, 114.7, 67.7, 31.3, 19.2, 13.9.

Workup

  1. customAfter 2 hours the reaction was quenched by addition of 20 ml of methanol
  2. filtrationA yellow solid was collected by filtration
  3. washwashed three times with methanol
  4. customto afford NMR-pure product in 0.92 g (82.9%)
  5. customyield

Sources & evidence

ORD record
ord-0abdfbbd7902478a82462f48b5e236f9
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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