Dimethylformamide → HCID 59157961, compound

HRID 523121Notes

Reaction equation

HRID 523121 reaction equation
P(Br)(Br)([Br:3])=O.CN(C=O)C.[Br:11][C:12]1[C:21]([I:22])=[CH:20][CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([CH2:23]O)=[CH:17]2>C(Cl)Cl>[Br:11][C:12]1[C:13]2[C:18](=[CH:17][C:16]([CH2:23][Br:3])=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:21]=1[I:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24613Phosphorus oxybromideHCID 59157962HCID 59157962, compound

Product 1

HCID 59157961HCID 59157961, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of POBr3 (662 mg, 2.3 mmol) in 4.5 mL of CH2Cl2 at 0° C. was added DMF (2.25 mL) dropwise. The reaction was stirred for 10 minutes and then a solution of (5-bromo-6-iodo-2-naphthyl)methanol (280 mg, 0.77 mmol) in 5 mL of CH2Cl2 was added. The reaction mixture was stirred for 30 minutes, quenched with a saturated solution of NH4Cl, extracted with EtOAc and dried over Na2SO4. The organic extracts were evaporated to dryness to afford the titled product which was used as such in the next step.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. customquenched with a saturated solution of NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe organic extracts were evaporated to dryness

Sources & evidence

ORD record
ord-59e34169af1444399d42c54cf6fbfc64
Source dataset
uspto-grants-2016_05
Patent number
US09334295B2

Reaction notes

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