(Diethylamino)sulfur trifluoride → 1-Bromo-4-chloro-3-fluoromethyl-2-fluorobenzene

HRID 2249372Notes

Reaction equation

HRID 2249372 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Br:10][C:11]1[C:12]([F:20])=[C:13]([CH2:18]O)[C:14]([Cl:17])=[CH:15][CH:16]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][F:7])[C:12]=1[F:20]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 59299314(3-Bromo-6-chloro-2-fluorophenyl)methanol

Product 1

HCID 688085881-Bromo-4-chloro-3-fluoromethyl-2-fluorobenzeneYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of diethylamino sulfur trifluoride (7.6 g, 0.047 mol) in methylene chloride (25 mL) was slowly added to (3-bromo-6-chloro-2-fluorophenyl) methanol (10.3 g, 0.043 mol) in methylene chloride (150 mL) at 0° C. The solution was stirred at ambient temperature for 1 hour. A saturated solution of sodium bicarbonate (100 mL) was cautiously added and the mixture extracted with methylene chloride (2×100 mL). The combined organic phases were dried (sodium sulfate) and concentrated. The dark residual oil was purified by chromatography (5% ethyl acetate in hexanes) to give 1-bromo-4-chloro-3-fluoromethyl-2-fluorobenzene (6.20 g, 0.024 mol): 1H NMR (CDCl3): δ 7.55(m, 1H) 7.18 (dd, 1H) 5.6 (d, 2H).

Workup

  1. extractionthe mixture extracted with methylene chloride (2×100 mL)
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe dark residual oil was purified by chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c2cc8051f1b643a0846e49e22a7aa995
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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