Ethanol → Ethyl 3-(bromophenyl)acetate

HRID 272649Notes

Reaction equation

HRID 272649 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:16][CH3:17])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11470552Ethyl 3-(bromophenyl)acetate

Conditions

Temperature
0 °C

Procedure

Commercially available 2-(3-bromophenyl)acetic acid (13 g 0.06 mol) was dissolved in ethanol (130 ml) and cooled to 0° C. Thionyl chloride (20 ml) was added drop wise. The mixture was heated to 85° C. over night. Reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The organic layer was washed with 10% NaHCO3, water, dried over anhydrous sodium sulfate and concentrated to give 13 g (88%) of A6.1a.

Workup

  1. temperatureThe mixture was heated to 85° C. over night
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic layer was washed with 10% NaHCO3, water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give 13 g (88%) of A6.1a

Sources & evidence

ORD record
ord-6a3d3dfa79a74701a1bb235fef6f8fa9
Source dataset
uspto-grants-2008_11
Patent number
US07456194B2

Reaction notes

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