N-bromobutanimide → 2-bromomethyl-6-methoxynaphthalene

HRID 974665Notes

Reaction equation

HRID 974665 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 110193292-METHOXY-6-METHYLNAPHTHALENE

Product 1

HCID 100377832-bromomethyl-6-methoxynaphthaleneYield 69.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
35 °C

Procedure

A solution of 2-methyl-6-methoxynaphthalene (4.lg, 23.8 mmole) and azoisobutyronitrile (80 mg) in dry carbon tetrachloride (30 ml) was heated to reflux with stirring. A slurry of N-bromosuccinimide (4.6 g, 25.8 mmole) and azoisobutyronitrile (20 mg) in dry carbon tetrachloride (10 ml) was added gradually over 2 hours. The resulting solution was heated under reflux for 30 minutes and then cooled to 35° C. The succinimide was filtered off and washed with carbon tetrachloride (5 ml). The filtrate was evaporated to dryness to afford a creamy coloured solid which was dried under vacuum at 40° C. It weighed 5.8 g and contained 70.3% 2-bromomethyl-6-methoxynaphthalene giving an activity yield of 69.5%.

Workup

  1. temperatureto reflux
  2. temperatureThe resulting solution was heated
  3. temperatureunder reflux for 30 minutes
  4. filtrationThe succinimide was filtered off
  5. washwashed with carbon tetrachloride (5 ml)
  6. customThe filtrate was evaporated to dryness
  7. customto afford a creamy coloured solid which
  8. customwas dried under vacuum at 40° C

Sources & evidence

ORD record
ord-2bcc8b676a6440c7b7f39d7c278d762e
Source dataset
uspto-grants-1991_11
Patent number
US05068458

Reaction notes

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