2-(4-Fluorophenyl)acetic acid → 4-Fluorophenylacetyl chloride

HRID 1401306Notes

Reaction equation

HRID 1401306 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:15])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:15])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 98372-(4-Fluorophenyl)acetic acidHCID 65578Oxalyl chloride

Product 1

HCID 37449884-Fluorophenylacetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluorophenylacetic acid (1) (25 g, 162 mmol) in DCM (75 mL) was added oxalyl chloride (28.4 mL, 324 mmol) and 34 drops of DMF. The mixture was stirred at r.t. for 1 h-2 h and concentrated to produce 2-(4-fluorophenyl)acetyl chloride (1a) (yellow oil) that was re-dissolved in toluene (100 mL). To this solution was added lead(II) thiocyanate (55.0 g, 170 mmol). The mixture was heated to reflux for 1.5 h-2 h, cooled down, filtered and the filtrate was concentrated. The residue was applied onto a silica gel pad (20 cm) and eluted with EtOAc/hexanes (1/9), to afford after evaporation of the solvents title compound 2 (31 g, 98% yield) as a yellow oil. MS (m/z): 228.1 (M+H+ MeOH). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.26-7.22 (m, 2H), 7.09-7.07 (m, 2H), 3.84 (s, 2H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-23d6fdce5e4846fdbd542f732c8c3d6a
Source dataset
uspto-grants-2014_12
Patent number
US08907091B2

Reaction notes

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