Triphenylphosphine → 6-(3-Bromomethyl-phenyl)-hexanoic Acid Methyl Ester

HRID 2117206Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]O)[CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:44])C(=O)C1>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][Br:44])[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-(3-hydroxymethyl-phenyl)-hexanoic acid methyl ester (587 mg, 2.48 mmol) in THF (10 mL) is added triphenylphosphine (716 mg, 2.73 mmol), stirred until homogeneous then cooled to 0° C. NBS (486 mg, 2.73 mmol) is added portionwise and the reaction mixture stirred for 45 min. The mixture is concentrated and the residue is purified by flash chromatography (eluting with 10% ethyl acetate/hexanes) to give 682 mg of title compound. 1H NMR (300 MHz, CDCl3) δ 7.23 (m, 3H), 7.10 (m, 1H), 4.48 (s, 2H), 3.66 (s, 3H), 2.60 (t, 2H), 2.31 (t, 2H), 1.63 (m, 4H), 1.37 (m, 2H).

Workup

stirringthe reaction mixture stirred for 45 min
concentrationThe mixture is concentrated
customthe residue is purified by flash chromatography (eluting with 10% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-d059dffbaaac4fffb2ff52fe97cdc11c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE040558E1

Reaction notes

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