Chlorotrimethylsilane → Methyl 3-(3-bromophenyl)prop-2-enoate

HRID 1107723

Reaction equation

HRID 1107723 reaction equation
[CH3:1][Si](Cl)(C)C.[Br:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH:10]=[CH:11][C:12]([OH:14])=[O:13]>CO>[Br:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[CH:10]=[CH:11][C:12]([O:14][CH3:1])=[O:13]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 362513-(3-Bromophenyl)acrylic acid

Product 1

HCID 610698Methyl 3-(3-bromophenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethylsilyl chloride (5.6 ml) was added dropwise to a stirred solution of m-bromocinnamic acid (5.0 g, 22 mmol) in methanol (110 ml). After 4 h, the mixture was evaporated to give product as a white solid, M+ 242; 360 MHz 1H n.m.r (CDCl3) 7.67 (1H, s), 7.60 (1H, d, J 16 Hz), 7.50 (1H, d, J 7.9 Hz), 7.43 (1H, d, J 7.9 Hz), 7.26 (1H, d, J 15.6 Hz), 6.43 (1H, d, J 16.1 Hz), 3.81 (3H, s).

Workup

  1. customthe mixture was evaporated
  2. customto give product as a white solid, M+ 242

Sources & evidence

ORD record
ord-07a2faf5289543c5be0565a4f1ea7d72
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Linked notes

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