2-Bromo-5-methoxybenzyl bromide → 3-Bis(tert-butoxycarbonyl)aminomethyl-4-bromoanisole

HRID 2416680Notes

Reaction equation

HRID 2416680 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10]Br.[NH:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[K]>CN(C)C=O>[C:23]([O:22][C:20]([N:12]([CH2:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[Br:1])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 35259512-Bromo-5-methoxybenzyl bromideHCID 86222903Imidodicarbonic acid, bis(1,1-dimethylethyl) ester, potassium salt

Product 1

HCID 226321523-Bis(tert-butoxycarbonyl)aminomethyl-4-bromoanisoleYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-3-bromomethylanisole (24 g, 86 mmol) and potassium di-tert-butyl iminodicarboxylate (24 g, 94 mmol) in dimethylformamide (200 mL) was stirred under argon at room temperature for 18 hr. The reaction was then concentrated under vacuum and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried(MgSO4), and concentrated. The residue was recrystallized from hexane to give the title compound (15 g, 42%) as a white solid: 1H NMR (CDCl3) δ 7.40 (d, J=8.6 Hz, 1 H), 6.68 (m, 2 H), 4.81(s, 2 H), 3.74 (s, 3 H) 1.44 (s, 18 H).

Workup

  1. concentrationThe reaction was then concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and brine, dried(MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-bf1b8820d2a04b1586ad7f0102bdfd21
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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