tert-Butanol → tert-Butyl (5-bromothiophen-3-yl)carbamate

HRID 2283716Notes

Reaction equation

HRID 2283716 reaction equation
C([N:3]([CH2:6]C)[CH2:4][CH3:5])C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[Br:25][C:26]1[S:27][CH:28]=C(C(O)=O)C=1.[CH3:34][C:35]([OH:38])([CH3:37])[CH3:36]>C1(C)C=CC=CC=1>[C:35]([O:38][C:6](=[O:15])[NH:3][C:4]1[CH:5]=[C:26]([Br:25])[S:27][CH:28]=1)([CH3:37])([CH3:36])[CH3:34]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 15759194tert-Butyl (5-bromothiophen-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (15 mL) and diphenylphosphoryl azide (16.5 mL) were added to a solution of the mixture of 2-bromothiophene-4-carboxylic acid obtained in the above-described Step (14.48 g) in toluene (250 mL) at room temperature. The reaction solution was stirred for 2 hours. 2-Methyl-2-propanol (40 mL) was added to the reaction solution, and then the reaction solution was stirred at 100° C. for 2 hours. The reaction solution was evaporated under vacuum, and the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain tert-butyl(5-bromothiophen-3-yl)carbamate as a white solid.

Workup

  1. stirringthe reaction solution was stirred at 100° C. for 2 hours
  2. customThe reaction solution was evaporated under vacuum
  3. customthe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8866f86e55044342b1339ab9a06f93e2
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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