Water → 4-(6-Bromonaphth-2-ylsulphonyl)phenol

HRID 346675Notes

Reaction equation

HRID 346675 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:10]=[CH:9]2.C(OCC)C.O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:10]=[CH:9]2

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 179157404-(6-Bromonaphth-2-ylsulphonyl)anisole

Product 1

HCID 179157994-(6-Bromonaphth-2-ylsulphonyl)phenolYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in methylene chloride (9.65 ml) was slowly added to a stirred, cooled (−78° C.), methylene chloride (25 ml) solution of a portion (1.21 g) of the anisole derivative so obtained. The mixture was stirred for 20 hours at ambient temperature, then cooled to −10° C., diethyl ether (4 ml) slowly added, and stirring continued for 10 minutes. Water (25 ml) was added and the mixture extracted with ethyl acetate (2×25 ml). The combined organic extracts were washed with water, dried (MgSO4) and evaporated. Trituration of the residue under ether gave 4-(6-bromonaphth-2-ylsulphonyl)phenol (1.03 g), m.p. 178-180° C.;

Workup

  1. customso obtained
  2. temperaturecooled to −10° C.
  3. stirringstirring
  4. waitcontinued for 10 minutes
  5. extractionthe mixture extracted with ethyl acetate (2×25 ml)
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-b94a525db2834c9da2468256997bc399
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

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