1,5-Dibromopentane → 3-(Bromopentyloxy)benzamide

HRID 1292139Notes

Reaction equation

HRID 1292139 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6]

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 3424033-Hydroxybenzamide

Product 1

HCID 183546093-(Bromopentyloxy)benzamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-hydroxybenzamide (0.5 g, 3.65 mmol), 1,5-dibromopentane (1.82 g, 1.1 ml, 7.3 mmol) and potassium carbonate (500 mg, 3.65 mmol) was refluxed (2h) in acetonitrile (18 ml) until the reaction was complete by TLC. The solvent was then removed by rotary evaporation to leave a white sticky solid which was chromatographed (10% methanol in dichloromethane on silica) to give a white solid. This was recrystallised from a mixture of petrol and ethyl acetate to give white flaky crystals (0.744 g, 2.6 mmol, 70% yield). mp 98°-99° C.

Workup

  1. customThe solvent was then removed by rotary evaporation
  2. customto leave a white sticky solid which
  3. customwas chromatographed (10% methanol in dichloromethane on silica)
  4. customto give a white solid
  5. customThis was recrystallised from a mixture of petrol and ethyl acetate

Sources & evidence

ORD record
ord-7bbe6dfb91a442deb2da1e497b5ec738
Source dataset
uspto-grants-1998_05
Patent number
US05756510

Reaction notes

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