4-Bromotoluene → HCID 10130667, compound

HRID 412764Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH2:9]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].CC(C)([O-])C.[Na+]>>[CH2:9]([N:13]([CH2:14][CH2:15][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH3:12]

Participants

Reactant 3

HCID 78054-Bromotoluene

HCID 8148Dibutylamine

HCID 23676156Sodium t-butoxide

Product 1

HCID 10130667HCID 10130667, compoundYield 93%

Procedure

According to the general procedure B, 4-bromotoluene (94 mg, 0.55 mmol) reacted with N,N-di-n-butylamine (65 mg, 0.50 mmol) using 1 mol % of catalyst and sodium tert-butoxide (58 mg, 0.60 mmol) at 40° C. for 24 h to give the title compound (102 mg, 93%) as a colorless oil: 1H-NMR (300 MHz, CDCl3): δ 7.07 (d, 2H, J=8.4 Hz), 6.64 (d, 2H, J=8.4 Hz), 3.28 (t, 4H, J=7.2 and 7.8 Hz), 2.30 (s, 3H), 1.60 (m, 4H), 1.40 (m, 4H), 1.00 (t, 6H, J=7.5 and 7.2 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 146.17, 129.67, 124.34, 112.19, 50.99, 29.41, 20.38, 20.12, 14.01. GC/MS(EI): m/z 219 (M+), 176, 134.

Workup

customat 40° C.
customfor 24 h

Sources & evidence

ORD record: ord-f381fa70aa394125b39799cf017a2e14
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562989B2

Reaction notes

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