Thionyl Chloride → HCID 58418822, compound

HRID 2267209Notes

Reaction equation

HRID 2267209 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:12][CH:13]([CH3:17])[C:14]([OH:16])=O.O=S(Cl)Cl>>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:9])([CH3:10])[CH3:11])[CH:5]=[C:4]2[C:3]=1[CH2:12][CH:13]([CH3:17])[C:14]2=[O:16]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 67402090HCID 67402090, compound

Product 1

HCID 58418822HCID 58418822, compoundYield 76%

Conditions

Temperature
40 °C

Procedure

A mixture of 3-(2-bromo-4-tert-butylphenyl)-2-methylpropanoic acid (46 g, 150 mmol) and SOCl2 (18 ml, 220 mmol) was stirred for 1 h at 40° C. The excess of SOCl2 was removed in vacuo. The residue was dissolved in CH2Cl2 (50 ml) and added at 0° C. to a suspension of 20 g AlCl3 in CH2Cl2 (200 ml). The reaction mixture was stirred overnight, poured into ice/water (500 g) containing 50 ml of conc. HCl. The organic phase was collected, washed with water, dried over MgSO4 and evaporated. The residue was distilled at 125-130° C. /0.5 torr giving 32 g (76%) of product.

Workup

  1. customThe excess of SOCl2 was removed in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (50 ml)
  3. additionadded at 0° C. to a suspension of 20 g AlCl3 in CH2Cl2 (200 ml)
  4. stirringThe reaction mixture was stirred overnight
  5. additionpoured into ice/water (500 g)
  6. additioncontaining 50 ml of conc. HCl
  7. customThe organic phase was collected
  8. washwashed with water
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. distillationThe residue was distilled at 125-130° C. /0.5 torr

Sources & evidence

ORD record
ord-e20f596214bd41f3a5415403fd7a0b35
Source dataset
uspto-grants-2010_12
Patent number
US07858717B2

Reaction notes

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