3-Bromobenzyl bromide → HCID 22117271, compound

HRID 1275909Notes

Reaction equation

HRID 1275909 reaction equation
C([Li])CCC.[CH3:6][C:7]1([CH3:23])[CH2:11][O:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH3:22])=[N:8]1.[Br:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br>O1CCCC1>[Br:24][C:25]1[CH:26]=[C:27]([CH2:28][CH2:22][C:13]2[CH:14]=[C:15]([C:18]([F:21])([F:19])[F:20])[CH:16]=[CH:17][C:12]=2[C:9]2[O:10][CH2:11][C:7]([CH3:23])([CH3:6])[N:8]=2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 699793-Bromobenzyl bromideHCID 22117250HCID 22117250, compoundHCID 178418339Butyllithium

Product 1

HCID 22117271HCID 22117271, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.6 ml of a 2.5M solution in hexanes) was added to the product of step (ii) (0.59 g) in tetrahydrofuran (15 ml) at -65° C. After 1.5 hours 3-bromobenzyl bromide (1.0 g) in tetrahydrofuran (6 ml) was added. The reaction was stirred at room temperature for 2 hours, partitioned between brine and ethyl acetate, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 10% ethyl acetate in isohexane. Yield 0.44 g.

Workup

  1. custompartitioned between brine and ethyl acetate
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customPurification
  5. washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-794cdc9e85a3482c9070feef78ae1f55
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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