Water → HCID 19900821, compound

HRID 1029769Notes

Reaction equation

HRID 1029769 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[C:6]([F:16])[CH:5]=1.O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C>[Br:1][C:11]1[S:10][C:9]([CH2:8][C:7]2[CH:14]=[CH:15][C:4]([Br:3])=[CH:5][C:6]=2[F:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 656671Sodium PyrosulfiteHCID 19900850HCID 19900850, compound

Product 1

HCID 19900821HCID 19900821, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.44 ml) in acetic acid (5 ml) was added during 10 minutes to a stirred solution of (4-bromo-2-fluorobenzyl)thiophene (2.33 g) in acetic acid (10 ml). The solution was stirred for 2 hours, then poured into a mixture of water (50 ml) and a 20% w/v solution of sodium metabisulphite (20 ml). The mixture was extracted with ether (2×50 ml), the combined extracts washed with water and saturated brine, and then dried (MgSO4). The solvent was removed by evaporation to give 2-bromo-5-(4-bromo-2-fluorobenzyl)thiophene as an oil; in 72% yield; NMR: 4.04(s,2H), 6.55(d,1H), 6.85(d,1H), 7.07(t,1H), 7.14-7.30(m,2H); m/e, (chemical ionisation) 348(M+); which was used without further purification.

Workup

  1. extractionThe mixture was extracted with ether (2×50 ml)
  2. washthe combined extracts washed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-22a16f51ab714a44b531f957f2491add
Source dataset
uspto-grants-1992_04
Patent number
US05102905

Reaction notes

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