Boron tribromide → 1-(6-Bromohexyl)-2,3-dihydroxybenzene

HRID 2108250Notes

Reaction equation

HRID 2108250 reaction equation
B(Br)(Br)Br.[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[C:13]=1[O:20]C>C(Cl)Cl>[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:13]=1[OH:20]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 149862831-(6-Bromohexyl)-2,3-dimethoxybenzene

Product 1

HCID 149862841-(6-Bromohexyl)-2,3-dihydroxybenzeneYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (266 mL. 0.266 mol 1M in methylene chloride) was added dropwise over 1 hour to a cooled (-65°) solution of 40.0 g (0.133 mol) of 1-(6-bromohexyl)-2,3-dimethoxybenzene in 800 mL of anhydrous methylene chloride which was stirred in an argon atmosphere. The cooling bath was then removed and the reaction mixture was stirred for 1.5 hours. After cooling in an ice bath, 100 mL of water and 50 mL of 3N HCl were added and the mixture was stirred for 2 hours. The organic layer was separated, dried and concentrated under reduced pressure to an oil which was purified by HPLC using 5% methanol-chloroform to yield 34.7 g of 1-(6-bromohexyl)-2,3-dihydroxybenzene as an oil.

Workup

  1. customThe cooling bath was then removed
  2. stirringthe reaction mixture was stirred for 1.5 hours
  3. temperatureAfter cooling in an ice bath
  4. addition100 mL of water and 50 mL of 3N HCl were added
  5. stirringthe mixture was stirred for 2 hours
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated under reduced pressure to an oil which
  9. customwas purified by HPLC

Sources & evidence

ORD record
ord-7cb92d1edfc6410dae27e22c57c46fd3
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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