Triethylamine → N-(2-hydroxy-5-bromophenyl)-3,3-dimethylbutyramide

HRID 48166

Reaction equation

HRID 48166 reaction equation
[C:1]([CH2:5][C:6](Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:9][C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[OH:17].C(N(CC)CC)C>C(OCC)C>[OH:17][C:11]1[CH:12]=[CH:13][C:14]([Br:16])=[CH:15][C:10]=1[NH:9][C:6](=[O:7])[CH2:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 3518402-Amino-4-Bromophenol

Product 1

HCID 22742126N-(2-hydroxy-5-bromophenyl)-3,3-dimethylbutyramideYield 31.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of tert-butylacetyl chloride (2.7 g, 0.020 mol) in diethyl ether (20 ml) was added dropwise to a solution of 2-amino-4bromophenol (3.8 g, 0.020 mol) and triethylamine (2.1 g, 0.020 mol) in diethyl ether (160 ml) and the mixture was stirred at room temperature for 3 hours. The mixture was filtered and the filtrate was evaporated in vacuo. Purification by flash column chromatography on silica gel, eluting initially with ethyl acetate:dichloromethane 1.5:98.5 and then with ethyl acetate:dichloromethane 2.5:97.5, gave N-(2-hydroxy-5-bromophenyl)-3,3-dimethylbutyramide (1.8 g).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customPurification by flash column chromatography on silica gel
  4. washeluting initially with ethyl acetate:dichloromethane 1.5:98.5

Sources & evidence

ORD record
ord-a4dae2ba05c94e56acd37a42b6eece85
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Linked notes

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