(E)-5-(4-bromo-3-fluorophenyl)pent-4-enoic acid → 5-(4-Bromo-3-fluorophenyl)pentanoic acid

HRID 1911030Notes

Reaction equation

HRID 1911030 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[F:15]>CC(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[F:15]

Participants

3

Reactant 1

HCID 86685428(E)-5-(4-bromo-3-fluorophenyl)pent-4-enoic acid

Product 1

HCID 710610425-(4-Bromo-3-fluorophenyl)pentanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (E)-5-(4-bromo-3-fluorophenyl)pent-4-enoic acid from step L1 (420 mg, 1.54 mmol) in 2-propanol (5 mL), was added sulfide platinum 5 weight % on carbon (100 mg, 0.513 mmol). The mixture was stirred under a hydrogen filled balloon for 3 h. The solid was filtered off. The filtrate concentrated in vacuo to afford 5-(4-bromo-3-fluorophenyl)pentanoic acid (400 mg, 1.45 mmol, 95% yield). 1H NMR (500 HMz, chloroform-d) δ 7.45 (dd, J=8.0, 7.4 Hz, 1H), 6.96 (dd, J=9.7, 1.9 Hz, 1H), 6.86 (dd, J=8.1, 1.5 Hz, 1H), 2.66-2.60 (m, 2H), 2.43-2.38 (m, 2H), 1.72-1.64 (m, 4H).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationThe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5d15d8f457c94724b733e929c3b1c3f8
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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