Undecanoic Acid → 11-(2,4-Difluorophenyl)undecanoic acid

Reaction equation

[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Br-].C(CCCCCCCCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.[F:46][C:47]1[CH:54]=[C:53]([F:55])[CH:52]=[CH:51][C:48]=1C=O>>[F:46][C:47]1[CH:54]=[C:53]([F:55])[CH:52]=[CH:51][C:48]=1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:13])=[O:12]

Participants

Reactant 3

HCID 8180Undecanoic Acid

HCID 737702,4-Difluorobenzaldehyde

HCID 18795071(9-Carboxynonyl)(triphenyl)phosphanium bromide

Product 1

HCID 6808927411-(2,4-Difluorophenyl)undecanoic acid

Procedure

By the similar procedure of synthesis of B4, compound B2 (2.76 g, 5.38 mmol) and 2,4-difluorobenzaldehyde (588 mg, 4.14 mmole) were used as starting materials to afford compound B15 (431 mg, 1.45 mmol, 35%) as off-white solids. mp: 56° C. 1H-NMR (CDCl3, 400 MHz) δ 7.05-7.13 (m, 1H), 6.70-6.79 (m, 2H), 2.66 (t, J=7.6 Hz, 2H), 2.31 (t, J=7.4 Hz, 2H), 1.50-1.62 (m, 4H), 1.26 (m, 12H). 13C-NMR (CDCl3, 100 MHz) δ 180.00, 162.19, 159.80, 130.90, 125.31, 110.69, 103.44, 34.11, 30.15, 29.44, 29.36, 29.33, 29.19, 29.16, 29.03, 28.41, 24.69. HRMS (ESI) calculated for C17H24F2O2Na [M+Na]+: 321.1642, found: 321.1637.