Thionyl bromide → 2-Bromomethyl-1-phenylnapthalene

HRID 1451500Notes

Reaction equation

HRID 1451500 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][C:8]=2[CH2:17]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Br)([Br:21])=O>C1(C)C=CC=CC=1>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][C:8]=2[CH2:17][Br:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 19974716(1-Phenyl-2-naphthyl)methanol

Product 1

HCID 123530222-Bromomethyl-1-phenylnapthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The above alcohol (2.3 g) was dissolved in toluene (10 ml) and thionyl bromide (1.0 ml) was added. The mixture was stirred at ambient temperature for 1 h, heated at reflux for 10 minutes and finally stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with toluene (75 ml), washed with a 10% sodium bicarbonate solution and dried (MgSO4). The solvent was evaporated in vacuo to give crude (1-phenyl-2-naphtyl) methylbromide.

Workup

  1. temperatureheated
  2. temperatureat reflux for 10 minutes
  3. stirringfinally stirred at ambient temperature for 30 minutes
  4. washwashed with a 10% sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-37b3be625f2848f2add56f5bd143fe46
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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