Water → HCID 28825877, compound

HRID 1500974Notes

Reaction equation

HRID 1500974 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[Br:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[Br:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[O:20][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 28825877HCID 28825877, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 4-(bromomethyl)benzoate (1 g, 4.4 mmol) in acetone (60 mL) were added 3-bromophenol (1 g, 5.8 mol) and potassium carbonate (1.24 g, 9 mmol). After stirring at 40° C. for 12 hours, the reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL). The organic layer was separated, washed with water (30 mL) and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1) to give methyl 4-((3-bromophenoxy)methyl)benzoate (1 g, 71.4%) as a white solid. LRMS (M+H+) m/z: calcd 320.00. found 320. 1H NMR (300 MHz, d6-DMSO): δ 7.98 (d, J=8.4 Hz, 2H), 7.57 (d, J=8.1 Hz, 2H), 7.28-7.22 (m, 2H), 7.15-7.12 (m, 1H), 7.05-7.01 (m, 1H), 5.23 (s, 2H), 3.84 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. customThe organic layer was separated
  3. washwashed with water (30 mL)
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-00d9b1a1a2d14b7e8e496e3a57f0fc4c
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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