HCID 21071775, compound → 7-Bromo-4-methyl-1-benzofuran

HRID 1372153Notes

Reaction equation

HRID 1372153 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH2:10][CH:11](OC)OC>ClC1C=CC=CC=1>[Br:1][C:2]1[C:3]2[O:9][CH:10]=[CH:11][C:4]=2[C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 21071775HCID 21071775, compound

Product 1

HCID 210718007-Bromo-4-methyl-1-benzofuranYield 75%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

To a 500 ml round bottom flask was added 15.6 g polyphosphoric acid (PPA) and anhydrous chlorobenzene (260 ml). The mixture was brought to reflux and 1-bromo-2-(2,2-dimethoxy-ethoxy)-4-methyl benzene (8.11 g, 29.5 mmol) in chlorobenzene (60 ml) was added dropwise over 2 h. The reaction was heated to reflux for 3 h, cooled to room temperature, passed through a silica plug and concentrated. Column chromatography (100% hexane) afforded 4.67 g (75%) of product as a white waxy solid: mp 32–33° C.; 1H NMR (300 MHz, DMSO-d6): δ 2.46 (3H, s), 7.02 (1H, d, J=7.9 Hz), 7.16 (1H, d, J=2.2 Hz), 7.43 (1H, d, J=7.9 Hz), 8.10 (1H, d, J=2.2 Hz); MS (EI) m/z 210 ([M+]).

Workup

  1. temperatureto reflux
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 3 h
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2c34d8a2ab1a4d87862a428de9de0338
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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