1,5-Dibromopentane → HCID 11131348, compound

HRID 1695319Notes

Reaction equation

HRID 1695319 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br>CC(C)=O>[CH3:13][O:12][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([O:8][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][Br:20])=[C:4]([O:5][CH3:6])[CH:3]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 11131348HCID 11131348, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl vanillate (9.109 g, 50 mmol) in acetone (200 mL) were added K2CO3 (27.64 g, 200 mmol) and 1,5-dibromopentane (20.4 mL, 150 mmol). The resulting mixture was heated to reflux. After 6 h, TLC showed no starting material left. The mixture was cooled to rt, and the solid was removed by filtration. The filtrate was concentrated. Purification by flash chromatography (silica gel, 8:2 hexanes/EtOAc) afforded 4-(5-bromopentyloxy)-3-methoxy-benzoic acid methyl ester 15 as white solid (13.65 g, 82%): 1HNMR (300 MHz, CDCl3) δ 1.60-1.66 (m, 2H), 1.85-1.97 (m, 4H), 3.42 (t, J=5.0 Hz, 2H), 3.87 (s, 3H), 3.89 (s, 3H), 4.06 (t, J=5.0 Hz, 2H), 6.85 (d, J=6.3 Hz, 1H), 7.52 (d, J=1.5 Hz, 1H), 7.63 (dd, J=6.3, 1.5 Hz, 1H); EIMS m/z 353 and 355 ([M]++Na).

Workup

  1. temperatureThe resulting mixture was heated to reflux
  2. waitleft
  3. customthe solid was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customPurification by flash chromatography (silica gel, 8:2 hexanes/EtOAc)

Sources & evidence

ORD record
ord-587bfbe1b2d94f6abd0f16e4f23be215
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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