Aluminum(III) Chloride → HCID 58418800, compound

HRID 557503Notes

Reaction equation

HRID 557503 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[CH:11][C:3]=1[CH2:4][CH:5]([CH2:9][CH3:10])[C:6](Cl)=[O:7].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]2[C:3]=1[CH2:4][CH:5]([CH2:9][CH3:10])[C:6]2=[O:7]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 58418749HCID 58418749, compound

Product 1

HCID 58418800HCID 58418800, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 116 g (0.35 mol) of 2-(2-bromo-4-tert-butylbenzyl)butanoyl chloride in 150 ml of dry dichloromethane was added dropwise to a suspension of 56.2 g (0.42 mol) of powdered AlCl3 in 500 ml of dry dichloromethane for 1.5 hours at 0° C. The resulting mixture was stirred overnight at room temperature and then poured on 500 cm3 of ice. The organic layer was separated, and the aqueous layer was extracted by 3×100 ml of dichloromethane. The combined organic extract was washed by saturated aqueous NaHCO3, dried over K2CO3, and evaporated to dryness. Fractional rectification of the residue gave 92.2 g (89%) of the title product, b.p. 142° C.-147° C./1 mm Hg. Anal. calc. for C15H19BrO: C, 61.03; H, 6.49. Found: C, 59.88; H, 6.37. 1H NMR (CDCl3): δ 7.80 (d, J=1.5 Hz, 1H, 5-H), 7.71 (d, J=1.5 Hz, 1H, 7-H), 3.22 (dd, J=17.4 Hz, J=7.6 Hz, 1H, 3-H), 2.75-2.62 (m, 2H, 3′-H and 2-H), 1.98 (m, 1H, CHH′Me), 1.55 (m, 1H, CHH′Me), 1.34 (s, 9H, tBu), 1.03 (t, J=1.4 Hz, CH2Me). 13C{1H} NMR (CDCl3): δ 208.4, 153.3, 150.7, 138.7, 135.1, 121.8, 119.3, 49.2, 35.0, 32.9, 31.2, 24.4, 11.5.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted by 3×100 ml of dichloromethane
  3. extractionThe combined organic extract
  4. washwas washed by saturated aqueous NaHCO3
  5. dry with materialdried over K2CO3
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-32dc1b4e172e4b9db7d5f3560d099c18
Source dataset
uspto-grants-2011_11
Patent number
US08058461B2

Reaction notes

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