Thionyl Chloride → 4-(2-Bromoethoxy)-3-fluorobenzoyl chloride

HRID 626133Notes

Reaction equation

HRID 626133 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[F:14].S(Cl)([Cl:17])=O>>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:17])=[O:10])=[CH:7][C:6]=1[F:14]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 896557994-(2-Bromoethoxy)-3-fluorobenzoic acid

Product 1

HCID 896561284-(2-Bromoethoxy)-3-fluorobenzoyl chlorideYield 93%

Procedure

4-(2-Bromoethoxy)-3-fluorobenzoic acid (1.08 g, 4.1 mmol) and thionyl chloride (10 mL) were refluxed for 7 h. The excess of thionyl chloride was removed by repeated evaporation with dry toluene in vacuo, giving 1.07 g (93% yield) subtitle compound as a brown oil. 1H NMR (400 MHz, CDCl3) δ 7.93 (d, J=8.8 Hz, 1H), 7.86 (d, J=11.2 Hz, 1H), 7.04 (dd, J=8.4 Hz, 8.4 Hz, 1H), 4.46 (t, J=6.4 Hz, 2H), 3.70 (t, J=6.4 Hz, 2H).

Workup

  1. customThe excess of thionyl chloride was removed
  2. customevaporation with dry toluene in vacuo

Sources & evidence

ORD record
ord-d495f58ca6cc4dd7ad2404002cba7d99
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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