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alpha-Bromo-o-fluorotoluene → 4-(2-fluorobenzyloxy)-N-(t-butoxycarbonyl)-N-(isopropyl)butylamine

HRID 1066809
Notes
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Reaction equation

HRID 1066809 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[CH:9]([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br>O1CCCC1.C(Cl)Cl>[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][O:16][CH2:15][CH2:14][CH2:13][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:9]([CH3:11])[CH3:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 21196070HCID 21196070, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 211960844-(2-fluorobenzyloxy)-N-(t-butoxycarbonyl)-N-(isopropyl)butylamineYield 77.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
-78 °C

Procedure

A solution of N-(t-butoxycarbonyl)-4-hydroxy-N-isopropylbutylamine (539 mg, 2.33 mmol) in tetrahydrofuran (11 ml) at −40° C. was treated with potassium t-butoxide (1 M in tetrahydrofuran, 2.54 ml, 2.54 mmol). After 40 minutes, the suspension was cooled to −78° C. and treated with a solution of 2-fluorobenzyl bromide (400 mg, 2.12 mmol) in tetrahydrofuran (4 ml). The reaciton was slowly warmed to room temperature and stirred for about five hours. The reaction was diluted with methylene chloride and washed with 1 M potassium carbonate and brine. The organic fraction was dried over sodium sulfate, filtered, and concentrated. The crude oil was purified by liquid chromatography to yield 555 mg (77%) of the title intermediate as a clear oil.

Workup

  1. temperatureThe reaciton was slowly warmed to room temperature
  2. washwashed with 1 M potassium carbonate and brine
  3. dry with materialThe organic fraction was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified by liquid chromatography

Sources & evidence

ORD record
ord-fe3ed01893d1435f9cdbf3b11a93bc67
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06245761B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes