Sodium Iodide → Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

HRID 1698859Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][OH:29].[I-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH2:26][CH2:27][CH2:28][OH:29])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of phenol 25 (8.80 g, 33.0 mmol) and 3-bromno-1-propanol (2.9 mL, 33 mmol) in acetonitrile (300 nL) was added solid cesium carbonate (12 g, 37 mmol). After stirring 16hrs at 50° C., more 3-bromo-1-propanol (3.3 mmol) and cesium carbonate (3.3 mmol) were added and the reaction stirred another 2 hrs. After adding more 3-bromo-1-propanol and cesium carbonate (3.3 mmol each) and sodium iodide (3.3 mmol), the reaction was stirred 30 minutes at 65° C., then cooled and filtered. The filtrate was evaporated in vacuo, the residue dissolved in ethyl acetate, washed with water, and the organic layer dried over Na2SO4 and filtered. The evaporated filtrate then gave product 26 (5.96 g 56%). 1H NMR (300 MHz, CDCl3) δ 7.63 (t, 1H, J=1.5 Hz), 7.48 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.46-7.31 (m, 5H), 7.09 (t, 1H, J=2.4 Hz), 5.35 (s, 2H), 4.14 (t, 2H, J =6.0 Hz), 3.85 (t, 2H, J=6.0 Hz), 2.05 (pentet, 2H, J=6.0 Hz).

Workup

stirringthe reaction stirred another 2 hrs
stirringthe reaction was stirred 30 minutes at 65° C.
temperaturecooled
filtrationfiltered
customThe filtrate was evaporated in vacuo
dissolutionthe residue dissolved in ethyl acetate
washwashed with water
dry with materialthe organic layer dried over Na2SO4
filtrationfiltered

Sources & evidence

ORD record: ord-1296ac4b59674eb2b02118fe501f2986
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344466B2

Reaction notes

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