Benzene, (3-bromopropoxy)- → HCID 90411367, compound

HRID 1427733Notes

Reaction equation

HRID 1427733 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[Cl-].[Cl-].[Al+3].[I:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:21]([C:20]2[CH:24]=[CH:25][C:17]([I:16])=[CH:18][CH:19]=2)=[O:22])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 68522Benzene, (3-bromopropoxy)-HCID 743734-Iodobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 90411367HCID 90411367, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of (3-bromopropoxy)benzene (44.4 g, 206 mmol) in DCM was added dropwise to a suspension of aluminum trichloride (27.5 g 206 mmol) and 4-iodobenzoyl chloride (50.0 g, 188 mmol) in anhydrous DCM (330 ml) at −78° C. ca. Reaction turned yellow and was allowed to warm to r.t. and stir for 4 hs. Upon completion, reaction was brought to 0° C., diluted with DCM, and quenched with 5% HCl. The organic layer was separated, washed additionally with brine, and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure and re-crystallized using EtOAc to afford 60.1 g (71.8% yield) of (4-(3-bromopropoxy)phenyl)(4-iodophenyl)methanone as grey solid.

Workup

  1. customReaction
  2. customUpon completion, reaction
  3. customwas brought to 0° C.
  4. customquenched with 5% HCl
  5. customThe organic layer was separated
  6. washwashed additionally with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. customre-crystallized

Sources & evidence

ORD record
ord-1a1444deefc54b268f641967dd711b47
Source dataset
uspto-grants-2015_01
Patent number
US08933261B2

Reaction notes

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