Butyl bromide → HCID 86725594, compound

HRID 514473Notes

Reaction equation

HRID 514473 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.Br[CH2:12][CH2:13][CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([O:8][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 3271485-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 86725594HCID 86725594, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Charged 5-chloro-2-(hydroxymethyl)phenol (965 mg, 6.09 mmol, PREPARATION 7), bromobutane (918 mmol, 6.70 mmol), K2CO3 (1.68 g, 12.19 mmol) and DMF (6 mL) to a sealed tube, and the mixture was heated to 100° C. overnight. After cooling to room temperature, the reaction mixture was poured into ice water, extracted with ethyl acetate twice, and the organic extract was washed with water, brine and dried with anhydrous Na2SO4. Solvent removed and the residue was purified by flash column chromatograph to give 600 mg of the title compound (46%). 1H NMR (300 MHz, CDCl3): δ 0.98 (3H, t, J=7.2 Hz), 1.46-1.56 (2H, m), 1.75-1.84 (2H, m), 2.23 (1H, t, J=6.0 Hz), 4.00 (2H, t, J=6.3 Hz), 4.64 (2H, d, J=6.3 Hz), 6.85 (1H, d, J=1.8 Hz), 6.91 (1H, dd, J=1.8 Hz, 8.1 Hz), 7.19 (1H, d, J=7.8 Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate twice
  3. extractionthe organic extract
  4. washwas washed with water, brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customSolvent removed
  7. customthe residue was purified by flash column chromatograph

Sources & evidence

ORD record
ord-df3867ce4c994aeb8607549af153008a
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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