2-Bromotoluene → HCID 9794453, compound

HRID 412762Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[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][CH:5]=[CH:4][C:3]=1[CH3:8])[CH2:10][CH2:11][CH3:12]

Participants

Reactant 3

HCID 72362-Bromotoluene

HCID 8148Dibutylamine

HCID 23676156Sodium t-butoxide

Product 1

HCID 9794453HCID 9794453, compoundYield 37%

Procedure

According to the general procedure B, 2-bromotoluene (171 mg, 1.00 mmol) reacted with N,N-di-n-butylamine (129 mg, 1.00 mmol) using 1 mol % of catalyst and sodium tert-butoxide (115 mg, 1.20 mmol) at 60° C. to give the title compound (79 mg, 37%) as an oil: 1H-NMR (300 MHz, CDCl3): δ 7.20-7.08 (m, 3H), 6.98 (app.t, 1H), 2.94 (t, 4H), 1.41 (m, 4H), 1.27 (m, 4H), 0.88 (t, 6H). GC/MS (EI): m/z 219 (M+).

Workup

customat 60° C.

Sources & evidence

ORD record: ord-7f7d1c2920c845cfa98fa11d1c24092a
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562989B2

Reaction notes

Loading…