Benzenepropanoic acid → beta-Bromobenzenepropanoic acid

HRID 66923

Reaction equation

HRID 66923 reaction equation
[C:1]([OH:11])(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl.O>[Br:12][CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][C:1]([OH:11])=[O:10]

Participants

7

Reactant 4

HCID 107Benzenepropanoic acidHCID 7187Benzoyl PeroxideHCID 11439SuccinimideHCID 67184N-bromobutanimide

Product 1

HCID 226117beta-Bromobenzenepropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 100 g (0.667 mol) of hydrocinnamic acid, 120 g (0.674 mol) of N-bromosuccinimide, and 1.8 g of benzoyl peroxide (BPO) in 900 ml of CCl4 was heated at reflux for 20 hr under nitrogen. After cooling to room temperature the reaction mixture was filtered. The filtrate when stripped to dryness yielded only a small amount of additional material which was combined with the original solid and the whole was slurried for 2 hr with warm water to dissolve the succinimide. The slurry was filtered and rinsed with water again and oven dried at 50° C. overnight to 120.8 g (79%) of material which is pure enough for the next step. Material recrystallized from toluene melts 138.5°-140.0° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr under nitrogen
  3. filtrationwas filtered
  4. customyielded only a small amount of additional material which
  5. filtrationThe slurry was filtered
  6. washrinsed with water again
  7. dry with materialoven dried at 50° C. overnight to 120.8 g (79%) of material which
  8. customMaterial recrystallized from toluene melts 138.5°-140.0° C.

Sources & evidence

ORD record
ord-02d0e14e6e874c8f85ccd141d69a175e
Source dataset
uspto-grants-1982_08
Patent number
US04343893

Linked notes

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