Water → HCID 86725604, compound

HRID 514485Notes

Reaction equation

HRID 514485 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.[OH-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.O>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([O:8][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 3271485-Chloro-2-(hydroxymethyl)phenol

Product 1

HCID 86725604HCID 86725604, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-chloro-2-(hydroxymethyl)phenol (943 mg, 5.95 mmol) and NaOH (3.5 mL, 6.54 mmol, 2M in water) in ethanol (10 mL) was added 4-(bromomethyl)-1-fluorobenzene (1.13 g, 5.95 mmol) slowly, the mixture was then stirred at room temperature overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic phase was collected and washed with water, brine, and dried with anhydrous Na2SO4. The solvent was removed to give 900 mg of the title compound (57%). 1H NMR (400 MHz, CDCl3): δ 2.08 (1H, t, J=6.4 Hz), 4.67 (2H, d, J=6.4 Hz), 5.05 (2H, s), 6.93 (1H, d, J=1.2 Hz), 6.96 (1H, dd, J=1.6 Hz, 8.0 Hz), 7.07-7.11 (2H, m), 7.25 (1H, d, J=6.0 Hz), 7.37-7.40 (2H, m).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was collected
  3. washwashed with water, brine
  4. dry with materialdried with anhydrous Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-22124f8a2f0540a99884e6dab001937e
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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