N-bromobutanimide → 4-Benzyloxy-2-bromo-5-methoxytoluene

HRID 1835408Notes

Reaction equation

HRID 1835408 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]([O:16][CH3:17])=[CH:11][C:12]([CH3:15])=[C:13]([Br:18])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 50675084-Benzyloxy-3-methoxy-toluene

Product 1

HCID 121515384-Benzyloxy-2-bromo-5-methoxytolueneYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-benzyloxy-3-methoxytoluene (8.0 g) was dissolved in dimethylformamide (30 ml and a dimethylformamide (15 ml) solution of N-bromosuccinimide (6.36 g) was dropwise added thereto, followed by stirring at room temperature for one night. The reaction solution was poured into ice water (400 ml), and crystals thus deposited were collected by filtration, adequately washed with water, and dried for one night to obtain 10.64 g of 4-benzyloxy-2-bromo-5-methoxytoluene (m.p. 110-111° C.) substantially quantitatively, and its structure was confirmed by nuclear magnetic resonance spectrum.

Workup

  1. filtrationthus deposited were collected by filtration
  2. washadequately washed with water
  3. customdried for one night

Sources & evidence

ORD record
ord-fb1f5485c36644659b903031103a68dd
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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