Acetyl chloride → 2-(4-Acetamidophenoxy)-4-bromobenzoic acid

HRID 425285Notes

Reaction equation

HRID 425285 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:19](Cl)(=[O:21])[CH3:20].C(N(CC)CC)C>C1COCC1>[C:19]([NH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 578392102-(4-Aminophenoxy)-4-bromobenzoic acid

Product 1

HCID 667022002-(4-Acetamidophenoxy)-4-bromobenzoic acidYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 2f (500 mg, 1.6 mmol) in 10 mL of THF was treated with acetyl chloride (0.15 mL, 2.08 mmol) and triethylamine (0.22 mL, 2.08 mmol). After stirring for 2.5 h the solid was collected. The filtrate was evaporated in vacuo to give 0.48 g of Compound 3f. MS m/z=331 (M+1).

Workup

  1. customwas collected
  2. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-08ac5051025f4172b6895cf01d729ee4
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Reaction notes

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