4-Bromobenzaldehyde → 11-(4-Bromophenyl)undecanoic acid

HRID 712931Notes

Reaction equation

[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[Br:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1>>[Br:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:36][CH:35]=1

Participants

Reactant 2

HCID 707414-Bromobenzaldehyde

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

Product 1

HCID 1312646511-(4-Bromophenyl)undecanoic acid

Procedure

By the similar procedure of synthesis of B10, compound B2 (330 mg, 0.643 mmol) and 4-bromobenzaldehyde (91.5 mg, 0.495 mmole) were used as starting materials to afford B18 (98.0 mg, 0.287 mmol, 58%) as off-white solids. mp: 91° C. 1H-NMR (CDCl3, 400 MHz) δ 7.37 (d, J=8.3 Hz, 1H), 7.02 (d, J=8.3 Hz, 2H), 2.53 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.5 Hz, 2H), 1.52-1.63 (m, 4H), 1.20-1.37 (m, 12H). 13C-NMR (CDCl3, 100 MHz) δ 179.94, 141.79, 141.79, 131.22, 130.14, 119.22, 35.31, 34.11, 31.27, 29.44, 29.38, 29.36, 29.19, 29.12, 29.03, 24.68. HRMS (ESI) calculated C17H26BrO2 [M+H]+: 341.1116, found: 341.1111.

Workup

customto afford B18 (98.0 mg, 0.287 mmol, 58%) as off-white solids

Sources & evidence

ORD record: ord-612098d545cf479e9b3e4fe21f7d6d1b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181292B2

Reaction notes

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