Octylbenzene → 2-Bromo-1-(4-octylphenyl)ethanone

HRID 526295

Reaction equation

HRID 526295 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Br:19][CH2:20][C:21](Br)=[O:22]>ClCCl>[Br:19][CH2:20][C:21]([C:8]1[CH:9]=[CH:10][C:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][CH:7]=1)=[O:22]

Participants

5

Reactant 3

HCID 16607OctylbenzeneHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 113013752-Bromo-1-(4-octylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

Aluminium chloride (4.80 g, 32.0 mmol, 1.0 eq.) and 1-phenyloctane (6.84 g, 32.0 mmol) were dissolved in dry dichloromethane (10 mL) and cooled to −10° C. A solution of bromoacetyl bromide (3.14 mL, 32.0 mmol, 1.0 eq.) in dichloromethane (12 mL) was added dropwise and the mixture was allowed to return to r.t. while stirring overnight. The mixture was slowly poured into ice water (100 mL) and the aqueous phase was extracted with dichloromethane (3×50 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The product was obtained as brown, highly viscous oil and was used in the next reaction without purification. Yield: 8.90 g (62%), purity: 69% (GC).

Workup

  1. customto return to r.t.
  2. extractionthe aqueous phase was extracted with dichloromethane (3×50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe product was obtained as brown, highly viscous oil
  6. customwas used in the next reaction without purification

Sources & evidence

ORD record
ord-6d3a4085d8c740b3aac33d204c4d0660
Source dataset
uspto-grants-2016_05
Patent number
US09345791B2

Linked notes

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