Dimethylformamide → 2-(4-Bromophenoxy)acetamide

HRID 1054733Notes

Reaction equation

HRID 1054733 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C[N:20](C=O)C>ClCCl>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([NH2:20])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 74657p-Bromophenoxyacetic acid

Product 1

HCID 3028642-(4-Bromophenoxy)acetamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-bromophenoxy)acetic acid (500 mg, 2.00 mmol) in dichloromethane (10 mL) and DMF (0.2 mL) was added 2 M oxalyl choride in methylene chloride (5 mL, 10 mmol). The reaction mixture was stirred at room temperature for 2 hours, and the solvent was removed under reduced pressure. Ammonium hydroxide (15 mL) was added dropwise via additional funnel. After addition, the mixture was extracted with EtOAc (3×20 mL). The combined organic layers were dried and concentrated in vacuo to give 2-(4-bromophenoxy)acetamide (350 mg, 70% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.37-7.35 (m, 2 H), 6.81-6.79 (m, 2 H), 4.59 (s, 2 H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionAmmonium hydroxide (15 mL) was added dropwise via additional funnel
  3. additionAfter addition
  4. extractionthe mixture was extracted with EtOAc (3×20 mL)
  5. customThe combined organic layers were dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55c2abcb2f684698bb235f78c63fe161
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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