Thionyl bromide → 4-(Bromomethyl)-3,5-difluoropyridine

HRID 578883Notes

Reaction equation

HRID 578883 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:10])[C:7]=1[CH2:8]O.S(Br)([Br:13])=O>C(Cl)Cl.CN(C=O)C>[Br:13][CH2:8][C:7]1[C:2]([F:1])=[CH:3][N:4]=[CH:5][C:6]=1[F:10]

Participants

5

Reactant 2

HCID 68176Thionyl bromideHCID 66815317(3,5-Difluoropyridin-4-yl)methanol

Product 1

HCID 668150974-(Bromomethyl)-3,5-difluoropyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

(3,5-Difluoro-4-pyridyl)methanol (6.11 g, 42.11 mmol) was dissolved in CH2Cl2 (140 mL). At 0° C. Thionyl bromide (3.589 mL, 46.32 mmol) was added slowly, then 1 drop of DMF was added: the solution turned yellow with gas evolution. The reaction mixture was stirred at rt for 1.5 h. It was quenched with 10 ml water. The pH was made basic (pH=9) with aq NaHCO3. The water layer was extracted 3 times with CH2Cl2. The combined organic layers were washed with brine. The organic phase was dried with Na2SO4, filtrated and the filtrate evaporated. The desired product was obtained as a brown liquid (9.68 g, lacrimator).

Workup

  1. customAt 0° C
  2. customIt was quenched with 10 ml water
  3. extractionThe water layer was extracted 3 times with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialThe organic phase was dried with Na2SO4
  6. filtrationfiltrated
  7. customthe filtrate evaporated

Sources & evidence

ORD record
ord-ea3b8cd878e34e4f8bdae6b7f8cf2e5c
Source dataset
uspto-grants-2015_05
Patent number
US09040708B2

Reaction notes

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