2-Chloroethanol → HCID 18687665, compound

HRID 1872849Notes

Reaction equation

HRID 1872849 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:4]=1O.COC1C=C(SC)C(F)=CC=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:43][CH2:44][CH2:45][OH:46].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[C:4]([O:46][CH2:45][CH2:44][Cl:43])=[CH:5][C:6]=1[F:10]

Participants

7

Reactant 5

HCID 342-ChloroethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18687664HCID 18687664, compound2×HCID 18687674HCID 18687674, compound2×

Product 1

HCID 18687665HCID 18687665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of a mixture of 2-methoxy-4,5-difluoro-phenol (Intermediate 55) and 2-methoxy-4-methylthio-5-fluoro-phenol (Intermediate 56) (0.66 g), triphenylphosphine (2.16 g), 2-chloroethanol (0.55 ml) in tetrahydrofuran (15 ml) was slowly added diethyl azodicarboxylate (1.3 ml). The reaction was stirred at room temperature for 2 hours. Tetrahydrofuran was removed under vacuum. Chromatography (10% ethyl acetate-hexanes) afforded 0.31 g of 1,2-difluoro-4-(2-chloroethoxy)-5-methoxy-benzene (Intermediate 57) as a white solid: mp 51-52° C.; MS EI m/e 222 (M+), and 0.1 g of 1-fluoro-2-methylthio-4-(2-chloroethoxy)-5-methoxy-benzene (Intermediate 62) as a white solid: mp 58-60° C.; MS EI m/e 250 (M+).

Workup

  1. customTetrahydrofuran was removed under vacuum

Sources & evidence

ORD record
ord-ca3c933160324cc0b0a3d5bd849e7fea
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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