Ammonium Chloride → HCID 17952680, compound

HRID 1394638Notes

Reaction equation

HRID 1394638 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([CH:11]([CH3:13])[CH3:12])[C:3]=1[O:14][CH2:15][CH3:16].C([Li])(C)(C)C.[Br:22][C:23]1[CH:24]=[CH:25][C:26]([F:31])=[C:27]([CH:30]=1)[CH:28]=[O:29].[Cl-].[NH4+]>COCCOC>[Br:22][C:23]1[CH:24]=[CH:25][C:26]([F:31])=[C:27]([CH:28]([C:2]2[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[C:4]([CH:11]([CH3:13])[CH3:12])[C:3]=2[O:14][CH2:15][CH3:16])[OH:29])[CH:30]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 17952785HCID 17952785, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 17952680HCID 17952680, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1-Bromo-2-ethoxy-3,5-diisopropyl-benzene (2.0 g, 7.01 mmol) was dissolved in ethylene glycol dimethyl ether (20 ml) and the mixture cooled to −78° C. t-Butyl lithium (8.66 ml, 1.7M, 14.7 mmol) dropwise to the mixture over 30 min., then the reaction was stirred for an additional 30 min. before 5-bromo-2-fluorobenzaldehyde (1.57 g, 7.71 mmol) was added in one portion. The reaction was allowed to warm to ambient temperature, then stirred overnight The mixture was poured into saturated ammonium chloride solution (100 mL), and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified flash column (5% ethyl acetate in hexanes) to give (5-bromo-2-fluoro-phenyl)-(2-ethoxy-3,5-diisopropyl-phenyl)-methanol, as a pale yellow oil (1.88 g, 66%). 1H NMR (250 MHz, CDCl3): δ 7.73 (dd, 1H, J=1.2, J=7.5), 7.42 (m, 1H), 7.11 (d, 1H, J=1.2), 6.95 (t, 1H, J=7.5), 6.85 (d, 1H, J=1.2), 6.35 (d, 1H, J=6.2), 3.84 (q, 2H, J=6.9), 3.30 (m, 1H), 3.07 (d, 1H, J=6.2), 2.85 (m, 1H), 1.47 (t, 3H, J=6.9), 1.25 (s, 6H), 1.20 (s, 6H). MS [EI+] 431, 433 (M+Na)+.

Workup

  1. additionwas added in one portion
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified flash column (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7ac9f87ac588404384d3120b9055087f
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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