Hydrogen Bromide → 2-(Bromomethyl)benzo[b]thiophene

HRID 83044

Reaction equation

HRID 83044 reaction equation
[BrH:1].[S:2]1[C:6]([CH2:7]O)=[CH:5][C:4]2[CH:9]=[CH:10][CH:11]=[CH:12][C:3]1=2.C(Cl)(Cl)Cl>C(O)(=O)C.ClCCl>[Br:1][CH2:7][C:6]1[S:2][C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[CH:5]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 6212ChloroformHCID 27763352-(Hydroxymethyl)benzo[b]thiophene

Product 1

HCID 136426052-(Bromomethyl)benzo[b]thiophene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

HBr in acetic acid (6 mL) was added to a suspension of benzo[b]thiophen-2-ylmethanol (1 g, 6.1 mmol) in dichloromethane (6 mL) at room temperature. The reaction mixture was stirred for 3 hours then diluted by addition of chloroform (20 mL). The organic phase was washed with a saturated solution of hydrogenocarbonate (20 mL), dried over sodium sulfate and concentrated to dryness. The title product was obtained as a yellow oil (1.3 g, quantitative).

Workup

  1. washThe organic phase was washed with a saturated solution of hydrogenocarbonate (20 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cad88e94e395451e94eedf3346eb5b50
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Linked notes

Loading…