Ammonia → Ethyl 2-(4-Bromo-2-chlorophenyl)acetate

HRID 387223Notes

Reaction equation

HRID 387223 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([Cl:12])[CH:3]=1.S(Cl)(Cl)=O.N.[CH2:18](O)[CH3:19]>>[CH2:18]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[Cl:12])[CH3:19]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 24386Thionyl ChlorideHCID 53403617(4-Bromo-2-chlorophenyl)acetic acid

Product 1

HCID 67119604Ethyl 2-(4-Bromo-2-chlorophenyl)acetate

Procedure

(4-Bromo-2-chlorophenyl)-acetic acid (18, 44.03 g, 0.18 mol) was dissolved in ethanol (440 mL) and thionyl chloride (44.0 mL, 0.61 mol) was added dropwise. The mixture was refluxed for 1 h, and evaporated. The residue was taken up in toluene and evaporated (2×100 mL). The crude oily product was dissolved in dichloromethane (300 mL) and washed with water (2×100 mL), dried over sodium sulfate, filtered and evaporated. The residue was dried in high vacuum (0.2 mmHg) at room temperature, solidifying to a light yellow low melting crystalline solid (45.5 g, 0.16 mol, 93%) ESMS m/z 294 [M+H+NH3]+; 1H NMR (300 MHz, CDCl3): δ 7.55 (d, J=2 Hz, 1H), 7.37 (dd, J=8, 2 Hz, 1H), 7.16 (d, J=8 Hz, 1H), 4.18 (q, J=7 Hz, 2H), 3.71 (s, 2H), 1.26 (t, J=7 Hz, 3H).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customevaporated
  3. customevaporated (2×100 mL)
  4. dissolutionThe crude oily product was dissolved in dichloromethane (300 mL)
  5. washwashed with water (2×100 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was dried in high vacuum (0.2 mmHg) at room temperature

Sources & evidence

ORD record
ord-577049f3661a4c888e30fcf5993285c1
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

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