N-(4-Methoxyphenyl)Acetamide → N-(3-bromo-4-methoxyphenyl)acetamide

HRID 2406414Notes

Reaction equation

HRID 2406414 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].[Br:13]Br.OS([O-])=O.[Na+]>C(O)(=O)C>[Br:13][C:9]1[CH:10]=[C:5]([NH:1][C:2]([CH3:4])=[O:3])[CH:6]=[CH:7][C:8]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 5827N-(4-Methoxyphenyl)AcetamideHCID 24408BromineHCID 23665763Sodium Bisulfite

Product 1

HCID 244158N-(3-bromo-4-methoxyphenyl)acetamideYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 10.0 g (60.5 mmol) of 4-acetaminoanisole (5) in 80 mL of acetic acid, was added dropwise 11.6 g (72.7 mmol) of bromine and maintaining internal temperature of the reaction below 50° C. After stirring for 1 h, the reaction mixture was poured into 400 mL of ice-water containing 1.2 g of NaHSO3. The mixture was stirred until yellow-red color disappeared and left at room temperature for overnight. The solid (product) was filtered, dried under vacuum at 70° C., and crystallized from ethanol to give 10.19 g (69% yield). 1H NMR (CDCl3) δ 7.67 (d, J=2.5 Hz, 1 H), 7.44 (dd, J=9, 2.5 Hz, 1 H), 7.1 (bs, 1 H, NH), 6.85 (d, J=9 Hz, 1 H), 3.87 (s, 3 H, OMe), 2.16 (s, 3 H, CH3).

Workup

  1. temperaturemaintaining internal
  2. customtemperature of the reaction below 50° C
  3. stirringThe mixture was stirred until yellow-red color
  4. waitleft at room temperature for overnight
  5. filtrationThe solid (product) was filtered
  6. customdried under vacuum at 70° C.
  7. customcrystallized from ethanol
  8. customto give 10.19 g (69% yield)

Sources & evidence

ORD record
ord-ae81fba3b1c34942860bb00d4b2de2bf
Source dataset
uspto-grants-2014_08
Patent number
US08809368B2

Reaction notes

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