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

HRID 850057Notes

Reaction equation

HRID 850057 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-d6c336f166cf4cf18571460dfe120f7d
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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