Potassium Carbonate → [4-Chloro-2-(cyclopropylmethoxy)phenyl]methanol

HRID 514456Notes

Reaction equation

HRID 514456 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[CH:12]([CH:14]1[CH2:16][CH2:15]1)O.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][CH:14]2[CH2:16][CH2:15]2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3271485-Chloro-2-(hydroxymethyl)phenolHCID 53647370Bromocyclopropylmethanol

Product 1

HCID 86725580[4-Chloro-2-(cyclopropylmethoxy)phenyl]methanolYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Charged 5-chloro-2-(hydroxymethyl)phenol (616 mg, 3.88 mmol, PREPARATION 7), bromocyclopropylmethanol (525 mg, 3.88 mmol), K2CO3 (1.07 g, 7.77 mmol) and DMF (6 mL) to a flask, purged with nitrogen and heated to 80° C. overnight. Poured into ice water, and extracted with ethyl acetate twice, and washed the organic phase with water twice, brine and dried with anhydrous Na2SO4, removed the solvent for silica gel chromatograph to give 108 mg of the title compound (13%). 1H NMR (400 MHz, CDCl3): δ 0.33-0.37 (2H, m), 0.63-0.68 (2H, m), 1.26-1.28 (1H, m), 3.84 (2H, d, J=7.2 Hz), 4.67 (2H, s), 4.86 (1H, s), 6.84 (1H, d, J=1.2 Hz), 6.91 (1H, dd, J=2.0 Hz, 8.0 Hz), 7.19 (1H, d, J=7.6 Hz).

Workup

  1. custompurged with nitrogen
  2. additionPoured into ice water
  3. extractionextracted with ethyl acetate twice
  4. washwashed the organic phase with water twice
  5. dry with materialbrine and dried with anhydrous Na2SO4
  6. customremoved the solvent for silica gel chromatograph

Sources & evidence

ORD record
ord-3e0df4d096ce4d8c87798068740605b8
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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