Trifluoroacetic acid → HCID 90310561, compound

HRID 1519145Notes

Reaction equation

HRID 1519145 reaction equation
[F:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:8]2(O)[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[O:13][CH3:14])[CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 90310642HCID 90310642, compound

Product 1

HCID 90310561HCID 90310561, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500 mL round-bottomed flask were added a stir bar, 1-(3-fluoro-2-methoxyphenyl)cyclobutanol (5.21 g, 26.6 mmol), dry DCM (250 mL), Et3SiH (39.0 mL, 244 mmol) and TFA (20 mL, 260 mmol). The resultant mixture was stirred at rt for 22 h before concentrating to dryness and subjecting the residue to FCC to give 1-cyclobutyl-3-fluoro-2-methoxybenzene as a pale-yellow oil (3.78 g, 79%). 1H NMR (600 MHz, CDCl3) δ 7.03-6.99 (m, 1H), 6.99-6.95 (m, 1H), 6.91 (m, 1H), 3.86 (d, J=1.6, 3H), 3.83-3.72 (m, 1H), 2.39-2.28 (m, 2H), 2.19-2.07 (m, 2H), 2.07-1.98 (m, 1H), 1.89-1.80 (m, 1H).

Workup

  1. additionTo a 500 mL round-bottomed flask were added a stir bar
  2. concentrationbefore concentrating to dryness

Sources & evidence

ORD record
ord-32ee6ee9b6a54cf5a69117a34664e082
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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