Oxalyl chloride → HCID 131720367, compound

HRID 1637579Notes

Reaction equation

HRID 1637579 reaction equation
C(Cl)(=O)C([Cl:4])=O.[F:7][C:8]1([CH:20]([CH3:24])[C:21](O)=[O:22])[CH2:13][CH:12]=[CH:11][CH:10]=[C:9]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O.C(Cl)Cl>[F:7][C:8]1([CH:20]([CH3:24])[C:21]([Cl:4])=[O:22])[CH2:13][CH:12]=[CH:11][CH:10]=[C:9]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 86609494HCID 86609494, compound

Product 1

HCID 131720367HCID 131720367, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, oxalyl chloride (3.8 g, 30 mmol) was combined with methylene chloride (30 mL). The resulting mixture was cooled to 0° C. and dimethylformamide (10 drops) was added. After 5 minutes of stirring a solution of 2-fluoro-α-methyl-biphenylacetic acid (3.0 g, 12 mmol) in methylene chloride (30 mL) was added dropwise over a 30 minute period. The reaction mixture was allowed to warm to room temperature and stirred overnight. The solvent was evaporated to give the product in a quantitative yield as a yellow solid. 1H NMR (CDCl3) δ: 1.58 (d, 3 H), 4.20 (q, 1 H), 7.11 (t, 2 H), 7.33-7.47 (m, 4 H), 7.54 (d, 2 H).

Workup

  1. additionwas added dropwise over a 30 minute period
  2. temperatureto warm to room temperature
  3. customThe solvent was evaporated
  4. customto give the product in a quantitative yield as a yellow solid

Sources & evidence

ORD record
ord-56a9d5b1f72b4daea64dadba7cc33551
Source dataset
uspto-grants-2000_03
Patent number
US06043233

Reaction notes

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