Allyl bromide → HCID 58110122, compound

HRID 1803184Notes

Reaction equation

HRID 1803184 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:24][CH:25]=[CH2:26]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:26][CH:25]=[CH2:24])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 882092,4-Dichlorophenylacetic acidHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 58110122HCID 58110122, compound

Procedure

Step AB (1): 2-(2,4-Dichlorophenyl)acetic acid was deprotonated with NaHMDS and reacted with 3-bromoprop-1-ene using a procedure analogous to Step AA (1) to afford 2-(2,4-dichlorophenyl)pent-4-enoic acid as a clear viscous oil. LC-MS (M−H)− 243.1. 1H NMR (500 MHz, chloroform-d) δ ppm 7.42 (d, J=2.14 Hz, 1 H) 7.31-7.36 (m, 1 H) 7.25 (dd, J=8.24, 2.14 Hz, 1 H) 5.67-5.77 (m, J=17.05, 10.19, 6.83, 6.83 Hz, 1 H) 5.07 (dd, J=17.09, 1.53 Hz, 1 H) 5.04 (d, J=10.38 Hz, 1 H) 4.26 (t, J=7.48 Hz, 1 H) 2.81 (dt, J=14.34, 7.17 Hz, 1 H) 2.55 (dt, J=14.57, 7.21 Hz, 1 H).

Sources & evidence

ORD record
ord-45a914bda5cb4cd8b0a0fb25d8ada02a
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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