Dimethylformamide → HCID 22591555, compound

HRID 2101462Notes

Reaction equation

HRID 2101462 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10]O)=[C:7]([CH3:12])[C:6]=2[CH:13]=1.P(Br)(Br)[Br:15].CN(C=O)C>CCOCC>[Br:15][CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][C:6]=2[C:7]=1[CH3:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24614Phosphorus tribromideHCID 22591563HCID 22591563, compound

Product 1

HCID 22591555HCID 22591555, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-chloro-3-methyl benzofuran 2-methanol (18.3 mmol, 3.6 g) in ether (200 mL) was cooled to 0° C. To this was added drop wise phosphorus tribromide (29.3 mmol, 7.9 g) and then DMF (2 mL). After allowing the reaction mixture to come to room temperature over three hours, the reaction was quenched with ice water (100 mL). The ether layer was collected, dried, filtered and the filtrate was evaporated to a yellow solid: 2-bromomethyl-5-chloro-3-methyl benzofuran (88%, 4.2 g); mp 81° C.-82° C.

Workup

  1. customthe reaction was quenched with ice water (100 mL)
  2. customThe ether layer was collected
  3. customdried
  4. filtrationfiltered
  5. customthe filtrate was evaporated to a yellow solid

Sources & evidence

ORD record
ord-c3d579932000448aa31a14d883bf893f
Source dataset
uspto-grants-2009_08
Patent number
US07572910B2

Reaction notes

Loading…