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

HRID 429165Notes

Reaction equation

HRID 429165 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 (2 h) 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-b5e4b0d6cc1a41bab6f761f7b152c5dd
Source dataset
uspto-grants-2001_11
Patent number
US06316455B1

Reaction notes

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