1,4-Dimethoxybenzene → HCID 80374555, compound

HRID 2368920Notes

Reaction equation

HRID 2368920 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1>O>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([C:19]2[CH:20]=[C:15]([O:14][CH3:13])[CH:16]=[CH:17][C:18]=2[O:21][CH3:22])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 90161,4-DimethoxybenzeneHCID 69571(3,4-Difluorophenyl)acetic acid

Product 1

HCID 80374555HCID 80374555, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

3,4-Difluorophenylacetic acid (3.0 g, 17.4 mmol) and 1,4-dimethoxybenzene (3.6 g, 26.1 mmol) in polyphosphoric acid (50 g) was heated at 72° C. for 3 h. The reaction was cooled to 50° C., and H2O (70 mL) was added. The resulting mixture was extracted with ethyl acetate (2×100 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified on a silica gel column to give 2-(3,4-difluorophenyl)-1-(2,5-dimethoxyphenyl)ethanone (1.3 g) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 7.40-7.25 (m, 2H), 7.14-7.10 (m, 3H), 7.08-7.7.03 (m, 1H), 4.29 (s, 2H), 3.86 (s, 3H), 3.73 (s, 3H).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-49114d9820094dccab6c0dacffcc42a2
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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