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

HRID 1013936Notes

Reaction equation

HRID 1013936 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-71d1d9238a764626986e284f12b34b53
Source dataset
uspto-grants-2011_07
Patent number
US07982042B2

Reaction notes

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