Pyrrolidine → 1-(4-Bromo-2-fluorobenzyl)pyrrolidine

HRID 1694398Notes

Reaction equation

HRID 1694398 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[C:9]([F:15])[CH:8]=1>C(#N)C>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:9]([F:15])[CH:8]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 222667231-(4-Bromo-2-fluorobenzyl)pyrrolidineYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

A 4-L RB flask, equipped a magnetic stirring bar was charged with pyrrolidine (363 g, 426 mL, 5.1 mol) and acetonitrile (2750 mL). The mixture was cooled with an ice bath to 10° C., then solid 4-bromo-2-fluorobenzylbromide (MATRIX, Cat. #: 1707, 375 g, 1.4 mol) was added in 6 portions, keeping temperature below 20° C. The mixture was stirred at RT for 4 h. The solvent was removed under vacuum. Then 2 L of sat. Na2CO3 aq. and 500 mL of water was added, and the mixture was extracted with DCM (3×700 mL). The extract was dried over Na2SO4 and evaporated. The resulting light yellow oil was distilled under vacuum (˜1 mm, bp. 125° C.) to give 324.5 g (90%) of the product as a colorless oil. LCMS (M+H): 258.5.

Workup

  1. customtemperature below 20° C
  2. customThe solvent was removed under vacuum
  3. additionThen 2 L of sat. Na2CO3 aq. and 500 mL of water was added
  4. extractionthe mixture was extracted with DCM (3×700 mL)
  5. dry with materialThe extract was dried over Na2SO4
  6. customevaporated
  7. distillationThe resulting light yellow oil was distilled under vacuum (˜1 mm, bp. 125° C.)

Sources & evidence

ORD record
ord-5d89c8324c174b509384eb152e3c9d57
Source dataset
uspto-grants-2012_04
Patent number
US08158673B2

Reaction notes

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