Triethylamine → 3-(2-Fluoro-biphenyl-4-yl)-acrylic acid ethyl ester

HRID 1387457Notes

Reaction equation

HRID 1387457 reaction equation
[F:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=[CH2:17].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:20]([O:19][C:15](=[O:18])[CH:16]=[CH:17][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:2]([F:1])[CH:7]=1)[CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 5210634-Bromo-2-fluoro-1,1'-biphenyl

Product 1

HCID 542096623-(2-Fluoro-biphenyl-4-yl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-fluoro-4-bromobiphenyl 13-1 (7.5 gm, 31.8 mmol), ethyl acrylate (4.3 mL), Pd(OAc)2 (0.714 gm, 3.2 mmol), tri-o-tolylphosphine (1.94 gm, 1.5 mmol) and triethylamine (12 mL) was heated to 100° C. in a sealed tube for 12 h. The reaction was cooled to room temperature and diluted with dichloromethane (40 mL). The organic solution was washed with 10% aq. citric acid (20 mL), satd. aq. NaHCO3, and brine (20 mL). The organic solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (95:5 to 90:10 hexanes/EtOAc) to give the acrylate ester 13-2 as a white solid.

Workup

  1. washThe organic solution was washed with 10% aq. citric acid (20 mL)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (95:5 to 90:10 hexanes/EtOAc)

Sources & evidence

ORD record
ord-df80ab97d6284e05be449343180fd8ea
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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