Ammonium Chloride → HCID 90013412, compound

HRID 576700Notes

Reaction equation

HRID 576700 reaction equation
[Cl:1][C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[C:9]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[CH3:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27366722-Chloro-3-(trifluoromethyl)benzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 90013412HCID 90013412, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 2-chloro-3-trifluoromethylbenzaldehyde (1 g, 4.8 mmol) in THF (16 mL) was added methylmagnesium bromide (3M in THF, 1.8 mL, 5.3 mmol). The reaction was allowed to warm to rt and stirred overnight. Saturated aqueous NH4Cl was added, and the mixture was extracted with EtOAc (×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford the desired product as a clear oil (1.1 g, 98%). 1H NMR (500 MHz, CDCl3) δ 7.86-7.82 (m, 1H), 7.62 (dd, J=7.8, 1.5 Hz, 1H), 7.40 (t, J=7.8 Hz, 1H), 5.40 (q, J=6.4 Hz, 1H), 2.14 (s, 1H), 1.50 (d, J=6.4 Hz, 3H).

Workup

  1. extractionthe mixture was extracted with EtOAc (×3)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c99b155ddc084b5eaa011d8146a779e8
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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