Dimethylformamide → HCID 22591555, compound

HRID 22753Notes

Reaction equation

HRID 22753 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-150ad250b0c5431f9c7fcdd267292a0a
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Reaction notes

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