Hydrochloric Acid → 2,1-Benzothiazol-7-ol

HRID 1973397Notes

Reaction equation

HRID 1973397 reaction equation
C[O:2][C:3]1[C:11]2[C:7](=[CH:8][S:9][N:10]=2)[CH:6]=[CH:5][CH:4]=1.Cl.Cl.COC1C2C(=CSN=2)C=CC=1.B(Br)(Br)Br>CCOCC.C(Cl)Cl>[OH:2][C:3]1[C:11]2[C:7](=[CH:8][S:9][N:10]=2)[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 122558027-Methoxy-2,1-benzisothiazoleHCID 21491447HCID 21491447, compound

Product 1

HCID 214914432,1-Benzothiazol-7-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

7-Methoxy-2,1-benzisothiazole was dissolved in ether and converted to the hydrochloride using dry hydrogen chloride gas. The 7-methoxy-2,1-benzisothiazole hydrochloride (6.0 g.) was refluxed 22 hours in a solution of 16 g. boron tribromide and 160 ml. methylene chloride to give 3.78 g. pure, yellow, crystalline 7-hydroxy-2,1-benzisothiazole, mp. 99°-100.5° after recrystallization from hexane. This structure was confirmed by nmr.

Workup

  1. custompure, yellow, crystalline 7-hydroxy-2,1-benzisothiazole, mp. 99°-100.5° after recrystallization from hexane

Sources & evidence

ORD record
ord-29bb1d2c20524980ad92a437f64b1594
Source dataset
uspto-grants-1976_12
Patent number
US03997548

Reaction notes

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