Boron Trichloride → HCID 57750760, compound

HRID 900987Notes

Reaction equation

HRID 900987 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:9]=[C:8]([CH2:10]OC)[S:7][C:6]=1[CH3:13].B(Cl)(Cl)[Cl:16]>ClCCl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:9]=[C:8]([CH2:10][Cl:16])[S:7][C:6]=1[CH3:13]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 57750762HCID 57750762, compound

Product 1

HCID 57750760HCID 57750760, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (5-methoxymethyl-2-methyl-thiophen-3-yl)-acetic acid methyl ester (2.2 g, 10.1 mmol) in dichloromethane (60 mL) is cooled to −65° C. and treated with boron trichloride (10.1 mL, 1.0 M, 10.1 mmol) dropwise via syringe. The mixture is allowed to warm to 0° C., poured into ice-water and extracted with dichloromethane (3×). The combined organic extracts are washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated in vacuo to give (5-chloromethyl-2-methyl-thiophen-3-yl)-acetic acid methyl ester (2.2 g, 99%) as an orange oil. 1H NMR (CDCl 3, 300 MHz) δ 6.90 (s, 1 H), 4.72 (s, 2 H), 3.70 (s, 3 H), 3.50 (s, 2 H), 2.38 (s, 3 H).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. washThe combined organic extracts are washed with saturated aq NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fe1d3cb050f484cb56cdc81ae9b567b
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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