5-Bromosalicylic acid → HCID 69208031, compound

HRID 2373833Notes

Reaction equation

HRID 2373833 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:12](Br)[CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:12]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:11][CH2:3][CH2:2][CH2:10][CH3:6])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 8002Butyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 69208031HCID 69208031, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-2-hydroxy-benzoic acid (2.21 g, 10 mmol), butyl bromide (3.46 g, 25 mmol), potassium carbonate (2.76 g, 20 mmol) and DMF (20 mL) was heated at 100° C. for 1 h. The reaction mixture was partitioned between ether (120 mL) and brine (100 mL). Ether layer was separated and washed again with brine (100 mL), dried over MgSO4. Purification by flash chromatography (ethyl acetate/hexanes 1:99, 1:19, 1:9) gave 5-Bromo-2-butoxy-benzoic acid butyl ester as yellow oil (1.648 g, 5.01 mmol).

Workup

  1. customThe reaction mixture was partitioned between ether (120 mL) and brine (100 mL)
  2. customEther layer was separated
  3. washwashed again with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. customPurification by flash chromatography (ethyl acetate/hexanes 1:99, 1:19, 1:9)

Sources & evidence

ORD record
ord-3f6205f956ed49babafb8792a485c53f
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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