1-(Bromomethyl)-4-(trifluoromethoxy)benzene → HCID 9887474, compound

HRID 1016288Notes

Reaction equation

HRID 1016288 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([CH2:12][CH2:11][C:10](=[O:13])[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[NH:7]2)[CH2:3][CH2:2]1.[F:18][C:19]([F:30])([F:29])[O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>C1COCC1>[F:18][C:19]([F:29])([F:30])[O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:1]2[CH2:6][CH2:5][C:4]3([CH2:12][CH2:11][C:10](=[O:13])[C:9]4[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=4[NH:7]3)[CH2:3][CH2:2]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 10130807HCID 10130807, compound

Product 1

HCID 9887474HCID 9887474, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of diamine 11 (5 mg, 0.022 mmol) in anhydrous THF (0.2 mL), KF-Celite (12.6 mg, 0.109 mmol), and 4-trifluoromethoxybenzyl bromide (5.22 μL, 0.033 mmol) was agitated at RT for 16 h. The reaction was filtered and piperidinomethyl polystyrene N-2-(mercaptoethyl) aminoethyl polystyrene (26 mg, 0.033 mmol) was added to the filtrate. The reaction was agitated for another 12 h and then filtered. The filtrate was concentrated to yield 18 (6 mg, 0.015 mmol, 68%) as an oil. LRMS: M+=403.

Workup

  1. filtrationThe reaction was filtered
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-05821a70c28d4269be10de094dd3ba37
Source dataset
uspto-grants-2002_11
Patent number
US06476019B1

Reaction notes

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