Ammonium Chloride → HCID 22662121, compound

HRID 392889Notes

Reaction equation

HRID 392889 reaction equation
C[Li].Br[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][C:5]=1[CH3:19].[Li]C(C)(C)C.[F:25][C:26]1[CH:42]=[CH:41][C:29]([CH2:30][C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=2[O:39][CH3:40])[CH:34]=[O:35])=[CH:28][CH:27]=1.[NH4+].[Cl-]>C(OCC)C.C1COCC1>[F:25][C:26]1[CH:42]=[CH:41][C:29]([CH2:30][C:31]2[CH:32]=[C:33]([CH:34]([OH:35])[C:4]3[C:9]([CH3:10])=[CH:8][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][C:5]=3[CH3:19])[CH:36]=[CH:37][C:38]=2[O:39][CH3:40])=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 22662122tert-Butyl (4-bromo-3,5-dimethylphenyl)carbamateHCID 22662127HCID 22662127, compoundHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22662121HCID 22662121, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.3 ml of methyllithium (2.1 mmol, 1.6 M in diethyl ether) are introduced into 1 ml of diethyl ether and, at −78° C., 600 mg (1.99 mmol) of tert-butyl 4-bromo-3,5-dimethylphenylcarbamate (Example IV) in 2 ml of diethyl ether/1 ml of THF are added. After 20 min, 1.53 ml of t-BuLi (2.6 mmol, 1.7 M in pentane) are added dropwise and the mixture is stirred at −78° C. for 30 min. 3-(4-Fluorobenzyl)-4-methoxybenzaldehyde dissolved in 3 ml of THF is added dropwise. After stirring at −78° C. for 1 h, aqueous NH4Cl solution is added. The mixture is diluted with diethyl ether and extracted with water, and the organic phase is dried and concentrated in a rotary evaporator. Chromatography (cyclohexane/ethyl acetate=6:1) affords 493 mg (46%) of tert-butyl 4-[[3-(4-fluorobenzyl)-4-methoxyphenyl](hydroxy)methyl]-3,5-dimethylphenylcarbamate.

Workup

  1. additionis added dropwise
  2. stirringAfter stirring at −78° C. for 1 h
  3. extractionextracted with water
  4. customthe organic phase is dried
  5. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-dac9b6fd7a8a4166ae68ab3edc2e01e0
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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