Potassium Bromide → 2-(Thiophen-2-yl)-1,3-thiazole-4-carbaldehyde

Reaction equation

CC1(C)N([O])C(C)(C)CCC1.[K+].[Br-].[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]1[S:20][CH:21]=[C:22]([CH2:24][OH:25])[N:23]=1.Cl[O-].[Na+].C([O-])(O)=O.[Na+]>O.C(Cl)Cl>[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]1[S:20][CH:21]=[C:22]([CH:24]=[O:25])[N:23]=1

Participants

Reactant 5

HCID 253877Potassium Bromide

HCID 516892Sodium Bicarbonate

HCID 2724126Tempo

HCID 2776319[2-(2-Thienyl)-1,3-thiazol-4-YL]methanol

HCID 23665760Sodium Hypochlorite

Product 1

HCID 184115512-(Thiophen-2-yl)-1,3-thiazole-4-carbaldehyde

Reagents, catalysts & solvents 2

Procedure

TEMPO (5.1 mg; 0.0329 mmol) and a solution of KBr (39.2 mg; 0.329 mmol) in water (0.5 ml) were added to a solution of (2-thiophen-2-ylthiazole-4-yl)methanol (0.65 g; 3.29 mmol) in CH2Cl2 (12 ml), followed, after cooling to 0-5° C., by dropwise addition of a solution of 7.1% sodium hypochlorite (4.1 ml; 4.1 mmol) and NaHCO3 (245 mg).

Sources & evidence

ORD record: ord-39b93f7759374974b15ce23454ff4d93
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06468979B1

Reaction notes

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