2-(2-Acetyl-5-bromophenoxy)acetic acid → 6-Bromo-3-methylbenzofuran

HRID 2170486Notes

Reaction equation

HRID 2170486 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:5]=1[O:6][CH2:7]C(O)=O)(=O)[CH3:2].C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[Br:15][C:12]1[CH:13]=[CH:14][C:4]2[C:1]([CH3:2])=[CH:7][O:6][C:5]=2[CH:11]=1

Participants

4

Reactant 2

HCID 2937532-(2-Acetyl-5-bromophenoxy)acetic acidHCID 517045Sodium Acetate

Product 1

HCID 123374986-Bromo-3-methylbenzofuranYield 75%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

A 100 mL flask equipped with a magnetic stirbar, condenser, is charged with 2-(2-acetyl-5-bromophenoxy)acetic acid (1.14 g, 4.0 mmol) and (40 mL) of acetic anhydride and sodium acetate (860 mg, 10 mmol). The mixture was heated at 80° C. for 2 hours. After cooling the reaction mixture was evaporated to dryness. (40 mL) of methanol was added followed by concentrating under vacuum to give 6-bromo-3-methylbenzofuran (600 mg, 75%) as yellow oil. 1H NMR (300 MHz, CD3OD) δ 7.62 (s, 1H), 7.38-7.36 (m, 3H), 2.23 (s, 3H).

Workup

  1. customA 100 mL flask equipped with a magnetic stirbar, condenser
  2. temperatureAfter cooling the reaction mixture
  3. customwas evaporated to dryness
  4. addition(40 mL) of methanol was added
  5. concentrationby concentrating under vacuum

Sources & evidence

ORD record
ord-0dff78871c2146e69fc1f5797c2d98ec
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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