1,4-Dimethoxybenzene → HCID 61992261, compound

HRID 714599Notes

Reaction equation

HRID 714599 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19](O)=[O:20])[CH:15]=[CH:16][CH:17]=1>O>[Br:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]([C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[O:9][CH3:10])=[O:20])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 90161,4-DimethoxybenzeneHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 61992261HCID 61992261, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

A mixture of 1,4-dimethoxybenzene (7.02 g, 50.8 mmol), 2-(3-bromophenyl)acetic acid (6.07 g, 28.2 mmol) and PPA (40 mL) was heated at 75° C. overnight and cooled to 50° C. Water (60 mL) was added, and the mixture was allowed to cool to room temperature. Additional water (100 mL) was added, and the mixture was extracted with DCM (2×200 mL). The organic phase was washed (100 mL H2O, 100 mL brine), dried (Na2SO4), and concentrated under reduced pressure. The crude material was purified on a silica gel column to give 2-(3-bromophenyl)-1-(2,5-dimethoxyphenyl)ethanone (6.12 g, 65%). 1H NMR (DMSO-d6): δ 7.45-7.41 (m, 2H), 7.29-7.24 (m, 1H), 7.23-7.19 (m, 1H), 7.13 (m, 2H), 7.11 (m, 1H), 4.29 (s, 2H), 3.87 (s, 3H), 3.73 (s, 3H); LCMS: 335.1 [M+H]+.

Workup

  1. temperaturecooled to 50° C
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted with DCM (2×200 mL)
  4. washThe organic phase was washed (100 mL H2O, 100 mL brine)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-b314fc1ba93a4e11ad98afa7948d08a4
Source dataset
uspto-grants-2015_11
Patent number
US09187460B2

Reaction notes

Loading…